dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-51058237535e457d9905830a9a214c22 | C#CCN(C)C(=O)N(C)C.COc1cc2c(Nc3c(Cl)cc(I)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1>>COc1cc2c(Nc3c(Cl)cc(C#CCN(C)C(=O)N(C)C)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | ClC1=C(C2=C(OCO2)C(=C1)I)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1.CN(C(=O)N(CC#C)C)C.C(C)(C)NC(C)C>>ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1)C#CCN(C(=O)N(C)C)C | [CH:13]#[C:14][CH2:15][N:16]([CH3:17])[C:18](=[O:19])[N:20]([CH3:21])[CH3:22].I[c:12]1[cH:11][c:9]([Cl:10])[c:8]([NH:7][c:6]2[c:5]3[cH:4][c:3]([O:2][CH3:1])[c:33]([O:34][CH2:35][CH2:36][CH2:37][N:38]4[CH2:39][CH2:40][O:41][CH2:42][CH2:43]4)[cH:32][c:31]3[n:30][cH:29][n:28]2)[c:24]2[c:23]1[O:27][CH2:26][O:25]2>>[CH3:1][... | C#CCN(C)C(=O)N(C)C.COc1cc2c(Nc3c(Cl)cc(I)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | COc1cc2c(Nc3c(Cl)cc(C#CCN(C)C(=O)N(C)C)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | null | [Cu]I.[Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | C(C)(=O)OCC | C-C Coupling | Sonogashira alkyne_aryl halide | 4fe05dd9f4e06ca437f6fd540183d70cbf88cbb037b34a93217c201e7139cd32 | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1cc(Nc2ncnc3cc(OCCCN4CCOCC4)ccc23)c2c(c1)OCO2 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1.[C:9]-[C:10]#[CH;D1;+0:11]>>[C:9]-[C:10]#[C;H0;D2;+0:11]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1 | 69 | [{"value": 69.0, "product": "ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1)C#CCN(C(=O)N(C)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.6, "product": "ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1)C#CCN(C(=O)N(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | null | null | 3 | HOUR | This was prepared using the method described in example 26 but it was carried out at room temperature over 3 hr using N-(5-chloro-7-iodo-1,3-benzodioxol-4-yl)-6-methoxy-7-(3-morpholin-4ylpropoxy)quinazolin-4-amine (310 mg, 0.52 mmol), N,N,N′-trimethyl-N′-prop-2-yn-1-ylurea (145 mg, 1.04 mmol), bis(triphenylphosphine) p... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2.c1ccc2ncncc2c1.C1COCC[NH]1 | HI | [Cu]I.[Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)(=O)OCC | null | 3 | C#CCN(C)C(=O)N(C)C.COc1cc2c(Nc3c(Cl)cc(I)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1>[Cu]I.[Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)(=O)OCC>COc1cc2c(Nc3c(Cl)cc(C#CCN(C)C(=O)N(C)C)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-57cfa8b9b39645b091a0818a65886850 | C#CCNC.O=C(Cl)Oc1ccc([N+](=O)[O-])cc1>>C#CCN(C)C(=O)Oc1ccc([N+](=O)[O-])cc1 | CNCC#C.C(C)N(CC)CC.ClC(=O)OC1=CC=C(C=C1)[N+](=O)[O-]>>CN(C(OC1=CC=C(C=C1)[N+](=O)[O-])=O)CC#C | [CH:1]#[C:2][CH2:3][NH:4][CH3:5].Cl[C:6](=[O:7])[O:8][c:9]1[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][cH:17]1>>[CH:1]#[C:2][CH2:3][N:4]([CH3:5])[C:6](=[O:7])[O:8][c:9]1[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][cH:17]1 | C#CCNC.O=C(Cl)Oc1ccc([N+](=O)[O-])cc1 | C#CCN(C)C(=O)Oc1ccc([N+](=O)[O-])cc1 | null | null | ClCCl | Protection | N-alkylation of secondary amines with alkyl halides | 496a200c7c2fc7c000296e03cda40efb8e258ccaeb02fa999285bf74ddc49346 | d86dc1e6d0e089b3444b62ddfcf4c4822bdac4b60e628553036562518c29adcd | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[c:4].[C;D1;H1:5]#[C:6]-[C:7]-[NH;D2;+0:8]-[C;D1;H3:9]>>[C;D1;H1:5]#[C:6]-[C:7]-[N;H0;D3;+0:8](-[C;D1;H3:9])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[c:4] | 89 | [{"value": 89.0, "product": "CN(C(OC1=CC=C(C=C1)[N+](=O)[O-])=O)CC#C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.5, "product": "CN(C(OC1=CC=C(C=C1)[N+](=O)[O-])=O)CC#C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | N-Methylpropargylamine (600 mg, 8.70 mmol) and triethylamine (878 mg, 8.68 mmol) in dichloromethane (10 ml) were added dropwise, with ice cooling, to a stirred solution of 4-nitrophenyl chloroformate (1.75 g, 8.68 mmol) in dichloromethane (10 ml). The reaction was stirred at ice temperature for 3 hr. then the resulting... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary amine | Carbamic ester | null | null | c1ccccc1 | HCl | ClCCl | null | 3 | C#CCNC.O=C(Cl)Oc1ccc([N+](=O)[O-])cc1>ClCCl>C#CCN(C)C(=O)Oc1ccc([N+](=O)[O-])cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-85f86d859ecf407a9e476f0021d732be | C#CCN(C)C(=O)Oc1ccc([N+](=O)[O-])cc1.CNC>>C#CCN(C)C(=O)N(C)C | CNC.CN(C(OC1=CC=C(C=C1)[N+](=O)[O-])=O)CC#C>>CN(C(=O)N(CC#C)C)C | O=[N+]([O-])c1ccc(O[C:6]([N:4]([CH2:3][C:2]#[CH:1])[CH3:5])=[O:7])cc1.[NH:8]([CH3:9])[CH3:10]>>[CH:1]#[C:2][CH2:3][N:4]([CH3:5])[C:6](=[O:7])[N:8]([CH3:9])[CH3:10] | C#CCN(C)C(=O)Oc1ccc([N+](=O)[O-])cc1.CNC | C#CCN(C)C(=O)N(C)C | null | null | ClCCl.C1CCOC1 | Acylation | OtherReaction | e2d977a702ed644c57a3c6a03e066457d8dc73a51640ae48afb0cf24b6adf835 | fc4b793bbeca2541e0488e7b2269d1dcbab20357be7785ff606aacdf4ebd8736 | null | O=[N+](-[O-])-c1:c:c:c(-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C;D1;H3:4])-[C:5]-[C:6]#[C;D1;H1:7]):c:c:1.[C;D1;H3:8]-[NH;D2;+0:9]-[C;D1;H3:10]>>[C;D1;H1:7]#[C:6]-[C:5]-[#7:3](-[C;D1;H3:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:9](-[C;D1;H3:8])-[C;D1;H3:10] | 46 | [{"value": 46.0, "product": "CN(C(=O)N(CC#C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | N-Methylpropargylamine (600 mg, 8.70 mmol) and triethylamine (878 mg, 8.68 mmol) in dichloromethane (10 ml) were added dropwise, with ice cooling, to a stirred solution of 4-nitrophenyl chloroformate (1.75 g, 8.68 mmol) in dichloromethane (10 ml). The reaction was stirred at ice temperature for 3 hr. then the resulting... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Nitro group.Secondary amine | Urea | c1ccccc1 | null | null | HO- | ClCCl.C1CCOC1 | null | null | C#CCN(C)C(=O)Oc1ccc([N+](=O)[O-])cc1.CNC>ClCCl.C1CCOC1>C#CCN(C)C(=O)N(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6455698656014bb88efa06f83549a201 | CN1CCNCC1=O.COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2>>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(C)C(=O)C4)c(OC)cc23)c2c1OCO2 | ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCCl.CN1C(CNCC1)=O>>ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CC(N(CC1)C)=O | [NH:23]1[CH2:24][CH2:25][N:26]([CH3:27])[C:28](=[O:29])[CH2:30]1.Cl[CH2:22][CH2:21][CH2:20][O:19][c:18]1[cH:17][c:16]2[n:15][cH:14][n:13][c:12]([NH:11][c:10]3[c:8]([Cl:9])[cH:7][c:6]([C:5]#[C:4][CH2:3][O:2][CH3:1])[c:37]4[c:36]3[O:40][CH2:39][O:38]4)[c:35]2[cH:34][c:31]1[O:32][CH3:33]>>[CH3:1][O:2][CH2:3][C:4]#[C:5][c:... | CN1CCNCC1=O.COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2 | COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(C)C(=O)C4)c(OC)cc23)c2c1OCO2 | null | null | COCCO | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1CN(CCCOc2ccc3c(Nc4cccc5c4OCO5)ncnc3c2)CCN1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1=[O;D1;H0:11]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5](-[C;D1;H3:4])-[C:10](=[O;D1;H0:11])-[C:9]-1 | 79 | [{"value": 79.0, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CC(N(CC1)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.0, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CC(N(CC1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This was prepared using the method described in example 13 using N-[5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-yl]-7-(3-chloropropoxy)-6-methoxyquinazolin-4-amine (250 mg, 0.51 mmol) and 1-methylpiperazin-2-one (290 mg, 2.54 mmol) in 2-methoxyethanol (4 ml). The crude product was purified by column chromato... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccc2ncncc2c1.C1C[NH]CC[NH]1.c1ccc2c(c1)OCO2 | HCl | COCCO | null | null | CN1CCNCC1=O.COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2>COCCO>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(C)C(=O)C4)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0dc265fd3757472a978addaf18056d89 | COCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCCl>>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCCl.ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)N.C[Si](C)(C)[N-][Si](C)(C)C.[Na+]>>ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCCl | [CH3:1][O:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][c:8]([Cl:9])[c:10]([NH2:11])[c:29]2[c:30]1[O:31][CH2:32][O:33]2.Cl[c:12]1[n:13][cH:14][n:15][c:16]2[cH:17][c:18]([O:19][CH2:20][CH2:21][CH2:22][Cl:23])[c:24]([O:25][CH3:26])[cH:27][c:28]12>>[CH3:1][O:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][c:8]([Cl:9])[c:10]([NH:11][c:12]2[n:13][cH:1... | COCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCCl | COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ncnc3ccccc23)c2c(c1)OCO2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:9]-[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13] | 66.6 | [{"value": 66.0, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCCl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.6, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCCl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This was prepared using the method described in example 4 using 4-chloro-7-(3-chloropropoxy)-6-methoxyquinazoline (400 mg, 1.39 mmol), 5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-amine (367 mg, 1.53 mmol) and sodium bis(trimethylsilyl)amide (1.0M in THF, 2.90 ml) in DMF (3 ml). The crude product was purified... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccc2c(c1)OCO2 | HCl | CN(C)C=O | null | null | COCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCCl>CN(C)C=O>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-846f11fc72ee4d4fa6b607c51158b70f | C#CCNC(=O)N(C)C.COc1cc2c(Nc3c(Cl)cc(I)c4c3OCO4)ncnc2cc1OCCCN1CCN(C)C(=O)C1>>COc1cc2c(Nc3c(Cl)cc(C#CCNC(=O)N(C)C)c4c3OCO4)ncnc2cc1OCCCN1CCN(C)C(=O)C1 | CN(C)C=O.ClC1=C(C2=C(OCO2)C(=C1)I)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CC(N(CC1)C)=O.CN(C(=O)NCC#C)C.CN(C(=O)NCC#C)C.C(C)(C)NC(C)C>>ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CC(N(CC1)C)=O)C#CCNC(N(C)C)=O | [CH:13]#[C:14][CH2:15][NH:16][C:17](=[O:18])[N:19]([CH3:20])[CH3:21].I[c:12]1[cH:11][c:9]([Cl:10])[c:8]([NH:7][c:6]2[c:5]3[cH:4][c:3]([O:2][CH3:1])[c:32]([O:33][CH2:34][CH2:35][CH2:36][N:37]4[CH2:38][CH2:39][N:40]([CH3:41])[C:42](=[O:43])[CH2:44]4)[cH:31][c:30]3[n:29][cH:28][n:27]2)[c:23]2[c:22]1[O:26][CH2:25][O:24]2>>... | C#CCNC(=O)N(C)C.COc1cc2c(Nc3c(Cl)cc(I)c4c3OCO4)ncnc2cc1OCCCN1CCN(C)C(=O)C1 | COc1cc2c(Nc3c(Cl)cc(C#CCNC(=O)N(C)C)c4c3OCO4)ncnc2cc1OCCCN1CCN(C)C(=O)C1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I | C(C)(=O)OCC | C-C Coupling | Sonogashira alkyne_aryl halide | 4fe05dd9f4e06ca437f6fd540183d70cbf88cbb037b34a93217c201e7139cd32 | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | O=C1CN(CCCOc2ccc3c(Nc4cccc5c4OCO5)ncnc3c2)CCN1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1.[C:9]-[C:10]#[CH;D1;+0:11]>>[C:9]-[C:10]#[C;H0;D2;+0:11]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1 | 66 | [{"value": 66.0, "product": "ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CC(N(CC1)C)=O)C#CCNC(N(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.7, "product": "ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CC(N(CC1)C)=O)C#CCNC(N(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_des... | null | null | 6 | HOUR | 4-[3-({4-[(5-Chloro-7-iodo-1,3-benzodioxol-4-yl)amino]-6-methoxyquinazolin-7-yl}oxy)propyl]-1-methylpiperazin-2-one (250 mg, 0.40 mmol) and N,N-dimethyl-N′-prop-2-yn-1-ylurea (60 mg, 0.48 mmol) in ethyl acetate (8 ml) stirred at room temperature, under an atmosphere of nitrogen, and treated with bis(triphenylphosphine)... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2.c1ccc2ncncc2c1.C1C[NH]CC[NH]1 | HI | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.C(C)(=O)OCC | null | 6 | C#CCNC(=O)N(C)C.COc1cc2c(Nc3c(Cl)cc(I)c4c3OCO4)ncnc2cc1OCCCN1CCN(C)C(=O)C1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.C(C)(=O)OCC>COc1cc2c(Nc3c(Cl)cc(C#CCNC(=O)N(C)C)c4c3OCO4)ncnc2cc1OCCCN1CCN(C)C(=O)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5cf72278c1fa4850a46bafb6034c8bcc | COCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1=O>>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(C)CC4=O)c(OC)cc23)c2c1OCO2 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1C(CN(CC1)C)=O.ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)N.C[Si](C)(C)[N-][Si](C)(C)C.[Na+]>>ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1C(CN(CC1)C)=O | [CH3:1][O:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][c:8]([Cl:9])[c:10]([NH2:11])[c:36]2[c:37]1[O:38][CH2:39][O:40]2.Cl[c:12]1[n:13][cH:14][n:15][c:16]2[cH:17][c:18]([O:19][CH2:20][CH2:21][CH2:22][N:23]3[CH2:24][CH2:25][N:26]([CH3:27])[CH2:28][C:29]3=[O:30])[c:31]([O:32][CH3:33])[cH:34][c:35]12>>[CH3:1][O:2][CH2:3][C:4]#[C:5][c:... | COCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1=O | COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(C)CC4=O)c(OC)cc23)c2c1OCO2 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1CNCCN1CCCOc1ccc2c(Nc3cccc4c3OCO4)ncnc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:9]-[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13] | 76 | [{"value": 76.0, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1C(CN(CC1)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.9, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1C(CN(CC1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This was prepared by the method described in example 4 using 1-{3-[(4-chloro-6-methoxyquinazolin-7-yl)oxy]propyl}-4-methylpiperazin-2-one (200 mg, 0.55 mmol), 5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-amine (145 mg, 0.60 mmol) and sodium bis(trimethylsilyl)amide (1.0M in THF, 1.15 ml) in DMF (3 ml). The cr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1C[NH]CC[NH]1.c1ccc2c(c1)OCO2 | HCl | CN(C)C=O | null | null | COCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1=O>CN(C)C=O>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(C)CC4=O)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-00e317efb747458091e0f9ae55df3bc9 | CC(C)(C)OC(=O)N1CCNC(=O)C1.CC(C)(C)[Si](C)(C)OCCCBr>>CC(C)(C)OC(=O)N1CCN(CCCO[Si](C)(C)C(C)(C)C)C(=O)C1 | BrCCCO[Si](C)(C)C(C)(C)C.O=C1CN(CCN1)C(=O)OC(C)(C)C.[OH-].[K+]>>[Si](C)(C)(C(C)(C)C)OCCCN1C(CN(CC1)C(=O)OC(C)(C)C)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][C:23](=[O:24])[CH2:25]1.Br[CH2:12][CH2:13][CH2:14][O:15][Si:16]([CH3:17])([CH3:18])[C:19]([CH3:20])([CH3:21])[CH3:22]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([CH2:12][CH2:13][CH2:14][O:15][Si:16]([CH3:17])(... | CC(C)(C)OC(=O)N1CCNC(=O)C1.CC(C)(C)[Si](C)(C)OCCCBr | CC(C)(C)OC(=O)N1CCN(CCCO[Si](C)(C)C(C)(C)C)C(=O)C1 | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | C1CCOC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 8deb65ebcb63ee1c4ed8a9ec85207ca3caec91658d1aafddbd37b9ca8c9c544a | 4a6c1e88c9e8bed487b746792f88d478ff36cc235f9a217d4632e6babdebdc9a | O=C1CNCCN1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[C:5]1-[C:6]-[#7:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:6]-[C:5]-1=[O;D1;H0:4] | 80 | [{"value": 80.0, "product": "[Si](C)(C)(C(C)(C)C)OCCCN1C(CN(CC1)C(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.0, "product": "[Si](C)(C)(C(C)(C)C)OCCCN1C(CN(CC1)C(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | (3-Bromopropoxy)-tert-butyldimethylsilane (2.53 g, 0.01 mol) in THF (10 ml) was added dropwise at room temperature to a stirred mixture of tert-butyl 3-oxopiperazine-1-carboxylate (2.0 g, 0.01 mol), powdered potassium hydroxide (0.67 g, 0.012 mol) and tetra-n-butylammonium bromide (0.63 g, 0.002 mol) in THF (15 ml). Th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | Tertiary amide | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1 | HBr | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C1CCOC1 | null | 2 | CC(C)(C)OC(=O)N1CCNC(=O)C1.CC(C)(C)[Si](C)(C)OCCCBr>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C1CCOC1>CC(C)(C)OC(=O)N1CCN(CCCO[Si](C)(C)C(C)(C)C)C(=O)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e1c1357707e24276ad6d34ac35b6ba18 | CC(C)(C)OC(=O)N1CCN(CCCO[Si](C)(C)C(C)(C)C)C(=O)C1>>O=C1CNCCN1CCCO | [Si](C)(C)(C(C)(C)C)OCCCN1C(CN(CC1)C(=O)OC(C)(C)C)=O.Cl>>OCCCN1C(CNCC1)=O | CC(C)(C)OC(=O)[N:4]1[CH2:3][C:2](=[O:1])[N:7]([CH2:8][CH2:9][CH2:10][O:11][Si](C)(C)C(C)(C)C)[CH2:6][CH2:5]1>>[O:1]=[C:2]1[CH2:3][NH:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH2:10][OH:11] | CC(C)(C)OC(=O)N1CCN(CCCO[Si](C)(C)C(C)(C)C)C(=O)C1 | O=C1CNCCN1CCCO | null | null | O1CCOCC1 | Reduction | OtherReaction | 75dc66e056407c5e7ed535d81c1ae346d0353e2bb9fcc19e693dd25e46cb4d4f | b7cd85816ce5be2fdff894ff2c2a341aaa3c3158d15ef465d974682e1c8a2e91 | O=C1CNCCN1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3](=[O;D1;H0:4])-[#7:5](-[C:6]-[C:7]-[C:8]-[O;H0;D2;+0:9]-[Si](-C)(-C)-C(-C)(-C)-C)-[C:10]-[C:11]-1>>[O;D1;H0:4]=[C:3]1-[C:2]-[NH;D2;+0:1]-[C:11]-[C:10]-[#7:5]-1-[C:6]-[C:7]-[C:8]-[OH;D1;+0:9] | 57.4 | [{"value": 57.0, "product": "OCCCN1C(CNCC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.4, "product": "OCCCN1C(CNCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | Tert-butyl 4-(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)-3-oxopiperazine-1-carboxylate (2.90 g, 7.8 mmol) in 1,4-dioxane (10 ml) was treated at room temperature with a 4N solution of HCl in 1,4-dioxane (15 ml) and the resulting solution stirred 4 hr then evaporated. The residue was taken up in a 10% methanol in dichloro... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.TMS ether protective group.Boc | Primary alcohol.Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | C1C[NH]CCN1 | HO- | O1CCOCC1 | null | 4 | CC(C)(C)OC(=O)N1CCN(CCCO[Si](C)(C)C(C)(C)C)C(=O)C1>O1CCOCC1>O=C1CNCCN1CCCO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-396e9a3822ac41f887a958e235c64d18 | C=O.O=C1CNCCN1CCCO>>CN1CCN(CCCO)C(=O)C1 | OCCCN1C(CNCC1)=O.C=O>>OCCCN1C(CN(CC1)C)=O | O=[CH2:1].[NH:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][OH:9])[C:10](=[O:11])[CH2:12]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][OH:9])[C:10](=[O:11])[CH2:12]1 | C=O.O=C1CNCCN1CCCO | CN1CCN(CCCO)C(=O)C1 | null | null | C(=O)O | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Secondary Amine Methylation | bebbbc2e5c9880d648b53dd51b2cf84a8e9c9861f8ae46f927ebe311ad1ddfb0 | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | O=C1CNCCN1 | O=[CH2;D1;+0:1].[C:2]-[#7:3]1-[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]-1=[O;D1;H0:9]>>[C:2]-[#7:3]1-[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH3;D1;+0:1])-[C:7]-[C:8]-1=[O;D1;H0:9] | 93 | [{"value": 93.0, "product": "OCCCN1C(CN(CC1)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4.5 | HOUR | 1-(3-Hydroxypropyl)piperazin-2-one (700 mg, 4.43 mmol) in formic acid (10 ml) and 37/40% aqueous formaldehyde solution (5 ml) was stirred and heated at 95° for 2 hr then the resulting solution evaporated in vacuo. The residue was taken up in 5% methanol in dichloromethane (20 ml), basified with a 7N solution of ammonia... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1 | Other | C(=O)O | null | 4.5 | C=O.O=C1CNCCN1CCCO>C(=O)O>CN1CCN(CCCO)C(=O)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-87f2eac24a9642afa6aba322e62d3679 | CN1CCN(CCCO)C(=O)C1.COc1cc2c(Cl)ncnc2cc1O>>COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1=O | CC(C)(C)OC(=O)/N=N/C(=O)OC(C)(C)C.ClC1=NC=NC2=CC(=C(C=C12)OC)O.OCCCN1C(CN(CC1)C)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.CC(C)(C)OC(=O)/N=N/C(=O)OC(C)(C)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1C(CN(CC1)C)=O | O[CH2:15][CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][N:21]([CH3:22])[CH2:23][C:24]1=[O:25].[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:7])[n:8][cH:9][n:10][c:11]2[cH:12][c:13]1[OH:14]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:7])[n:8][cH:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][N:21]([C... | CN1CCN(CCCO)C(=O)C1.COc1cc2c(Cl)ncnc2cc1O | COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1=O | null | null | ClCCl | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | O=C1CNCCN1CCCOc1ccc2cncnc2c1 | O-[CH2;D2;+0:1]-[C:2]-[C:3].[#7;a:4]:[c:5]:[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[#7;a:4]:[c:5]:[c:6]:[c:7](-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:9] | 50.2 | [{"value": 50.0, "product": "ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1C(CN(CC1)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.2, "product": "ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1C(CN(CC1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Di-tert-butylazodicarboxylate (393 mg, 1.71 mmol) was added portionwise, at room temperature, to a stirred suspension of 4-chloro-6-methoxyquinazolin-7-ol, (300 mg, 1.42 mmol), 1-(3-hydroxypropyl)-4-methylpiperazin-2-one (270 mg, 1.57 mmol) and triphenylphosphine (522 mg, 1.99 mmol) in dichloromethane (10 ml). The reac... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccc2ncncc2c1.C1C[NH]CC[NH]1 | HO- | ClCCl | null | 1 | CN1CCN(CCCO)C(=O)C1.COc1cc2c(Cl)ncnc2cc1O>ClCCl>COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bf4db140b7df4746b7c3b4edc6505413 | COCCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1=O>>COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(C)CC4=O)c(OC)cc23)c2c1OCO2 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1C(CN(CC1)C)=O.ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)N.C[Si](C)(C)[N-][Si](C)(C)C.[Na+]>>ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1C(CN(CC1)C)=O | [CH3:1][O:2][CH2:3][CH2:4][C:5]#[C:6][c:7]1[cH:8][c:9]([Cl:10])[c:11]([NH2:12])[c:37]2[c:38]1[O:39][CH2:40][O:41]2.Cl[c:13]1[n:14][cH:15][n:16][c:17]2[cH:18][c:19]([O:20][CH2:21][CH2:22][CH2:23][N:24]3[CH2:25][CH2:26][N:27]([CH3:28])[CH2:29][C:30]3=[O:31])[c:32]([O:33][CH3:34])[cH:35][c:36]12>>[CH3:1][O:2][CH2:3][CH2:4... | COCCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1=O | COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(C)CC4=O)c(OC)cc23)c2c1OCO2 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1CNCCN1CCCOc1ccc2c(Nc3cccc4c3OCO4)ncnc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:9]-[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13] | 67.8 | [{"value": 67.0, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1C(CN(CC1)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.8, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1C(CN(CC1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | null | null | null | null | This was prepared by the method described in example 4 but using 1-{3-[(4-chloro-6-methoxyquinazolin-7-yl)oxy]propyl}-4-methylpiperazin-2-one (140 mg, 0.38 mmol), 5-chloro-7-(4-methoxybut-1-yn-1-yl)-1,3-benzodioxol-4-amine (107 mg, 0.42 mmol) and sodium bis(trimethylsilyl)amide (1.0M in THF, 0.81 ml) in DMF (2 ml). The... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1C[NH]CC[NH]1.c1ccc2c(c1)OCO2 | HCl | CN(C)C=O | null | null | COCCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1=O>CN(C)C=O>COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(C)CC4=O)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cbc5759bd06e4d7e9967c05197de00e0 | CN(C)C(=O)NCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1=O>>COc1cc2c(Nc3c(Cl)cc(C#CCNC(=O)N(C)C)c4c3OCO4)ncnc2cc1OCCCN1CCN(C)CC1=O | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1C(CN(CC1)C)=O.NC1=C(C=C(C2=C1OCO2)C#CCNC(N(C)C)=O)Cl.C[Si](C)(C)[N-][Si](C)(C)C.[Na+]>>ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1C(CN(CC1)C)=O)C#CCNC(N(C)C)=O | [NH2:7][c:8]1[c:9]([Cl:10])[cH:11][c:12]([C:13]#[C:14][CH2:15][NH:16][C:17](=[O:18])[N:19]([CH3:20])[CH3:21])[c:22]2[c:23]1[O:24][CH2:25][O:26]2.Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:32]([O:33][CH2:34][CH2:35][CH2:36][N:37]3[CH2:38][CH2:39][N:40]([CH3:41])[CH2:42][C:43]3=[O:44])[cH:31][c:30]2[n:29][cH:28][n:27]1>>[... | CN(C)C(=O)NCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1=O | COc1cc2c(Nc3c(Cl)cc(C#CCNC(=O)N(C)C)c4c3OCO4)ncnc2cc1OCCCN1CCN(C)CC1=O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1CNCCN1CCCOc1ccc2c(Nc3cccc4c3OCO4)ncnc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:9]-[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13] | 81.4 | [{"value": 81.0, "product": "ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1C(CN(CC1)C)=O)C#CCNC(N(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.4, "product": "ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1C(CN(CC1)C)=O)C#CCNC(N(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_des... | null | null | null | null | This was prepared by the method described in example 4 but using 1-{3-[(4-chloro-6-methoxyquinazolin-7-yl)oxy]propyl}-4-methylpiperazin-2-one (140 mg, 0.38 mmol), N′-[3-(7-amino-6-chloro-1,3-benzodioxol-4-yl)prop-2-yn-1-yl]-N,N-dimethylurea (125 mg, 0.42 mmol) and sodium bis(trimethylsilyl)amide (1.0M in THF, 0.81 ml) ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2c(c1)OCO2.c1ccc2ncncc2c1.C1C[NH]CC[NH]1 | HCl | CN(C)C=O | null | null | CN(C)C(=O)NCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1=O>CN(C)C=O>COc1cc2c(Nc3c(Cl)cc(C#CCNC(=O)N(C)C)c4c3OCO4)ncnc2cc1OCCCN1CCN(C)CC1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7a2cbf012f724f2388fe0b5420a11e4c | COC(C)CC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1>>COc1cc2c(Nc3c(Cl)cc(C#CCC(C)OC)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1.ClC1=C(C2=C(OCO2)C(=C1)C#CCC(C)OC)N.C[Si](C)(C)[N-][Si](C)(C)C.[Na+]>>ClC1=C(C2=C(OCO2)C(=C1)C#CCC(C)OC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1 | [NH2:7][c:8]1[c:9]([Cl:10])[cH:11][c:12]([C:13]#[C:14][CH2:15][CH:16]([CH3:17])[O:18][CH3:19])[c:20]2[c:21]1[O:22][CH2:23][O:24]2.Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:30]([O:31][CH2:32][CH2:33][CH2:34][N:35]3[CH2:36][CH2:37][O:38][CH2:39][CH2:40]3)[cH:29][c:28]2[n:27][cH:26][n:25]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[... | COC(C)CC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1 | COc1cc2c(Nc3c(Cl)cc(C#CCC(C)OC)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ncnc3cc(OCCCN4CCOCC4)ccc23)c2c(c1)OCO2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:9]-[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13] | 64.3 | [{"value": 64.0, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCC(C)OC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.3, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCC(C)OC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This was prepared by the method described in example 4 but using 4-chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline (200 mg, 0.59 mmol), 5-chloro-7-(4-methoxypent-1-yn-1-yl)-1,3-benzodioxole-4-amine (174 mg, 0.65 mmol) and sodium bis(trimethylsilyl)amide (1.0M in THF, 1.24 ml) in DMF (3 ml). The crude product wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2c(c1)OCO2.c1ccc2ncncc2c1.C1COCC[NH]1 | HCl | CN(C)C=O | null | null | COC(C)CC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1>CN(C)C=O>COc1cc2c(Nc3c(Cl)cc(C#CCC(C)OC)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-64136a8cd324442f9a988bcc15cbb60e | C#CCC(C)OC.Nc1c(Cl)cc(I)c2c1OCO2>>COC(C)CC#Cc1cc(Cl)c(N)c2c1OCO2 | ClC1=C(C2=C(OCO2)C(=C1)I)N.COC(CC#C)C.C(C)(C)NC(C)C>>ClC1=C(C2=C(OCO2)C(=C1)C#CCC(C)OC)N | [CH3:1][O:2][CH:3]([CH3:4])[CH2:5][C:6]#[CH:7].I[c:8]1[cH:9][c:10]([Cl:11])[c:12]([NH2:13])[c:14]2[c:15]1[O:16][CH2:17][O:18]2>>[CH3:1][O:2][CH:3]([CH3:4])[CH2:5][C:6]#[C:7][c:8]1[cH:9][c:10]([Cl:11])[c:12]([NH2:13])[c:14]2[c:15]1[O:16][CH2:17][O:18]2 | C#CCC(C)OC.Nc1c(Cl)cc(I)c2c1OCO2 | COC(C)CC#Cc1cc(Cl)c(N)c2c1OCO2 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I | C(C)(=O)OCC | C-C Coupling | Sonogashira alkyne_aryl halide | 4fe05dd9f4e06ca437f6fd540183d70cbf88cbb037b34a93217c201e7139cd32 | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccc2c(c1)OCO2 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1.[C:9]-[C:10]#[CH;D1;+0:11]>>[C:9]-[C:10]#[C;H0;D2;+0:11]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1 | 92 | [{"value": 92.0, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCC(C)OC)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.5, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCC(C)OC)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 90 | MINUTE | 5-chloro-7-iodo-1,3-benzodioxol-4-amine (600 mg, 2.02 mmol) and 4-methoxypent-1-yne (500 mg, 5.10 mmol) in ethyl acetate (8 ml) were cooled in ice-methanol, under an atmosphere of nitrogen, then treated with bis(triphenylphosphine)palladium(II) dichloride (141 mg, 10 mol %) followed by copper(I) iodide (38 mg, 10 mol %... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | HI | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.C(C)(=O)OCC | null | 1.5 | C#CCC(C)OC.Nc1c(Cl)cc(I)c2c1OCO2>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.C(C)(=O)OCC>COC(C)CC#Cc1cc(Cl)c(N)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0a3ac54f66474a0b88147a0694c6ec41 | C#CCC(C)OC.COc1cc2c(Nc3c(Cl)cc(I)c4c3OCO4)ncnc2cc1OCCCN1CCN(C)C(=O)C1>>COc1cc2c(Nc3c(Cl)cc(C#CCC(C)OC)c4c3OCO4)ncnc2cc1OCCCN1CCN(C)C(=O)C1 | CN(C)C=O.ClC1=C(C2=C(OCO2)C(=C1)I)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CC(N(CC1)C)=O.COC(CC#C)C.COC(CC#C)C.C(C)(C)NC(C)C>>ClC1=C(C2=C(OCO2)C(=C1)C#CCC(C)OC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CC(N(CC1)C)=O | [CH:13]#[C:14][CH2:15][CH:16]([CH3:17])[O:18][CH3:19].I[c:12]1[cH:11][c:9]([Cl:10])[c:8]([NH:7][c:6]2[c:5]3[cH:4][c:3]([O:2][CH3:1])[c:30]([O:31][CH2:32][CH2:33][CH2:34][N:35]4[CH2:36][CH2:37][N:38]([CH3:39])[C:40](=[O:41])[CH2:42]4)[cH:29][c:28]3[n:27][cH:26][n:25]2)[c:21]2[c:20]1[O:24][CH2:23][O:22]2>>[CH3:1][O:2][c:... | C#CCC(C)OC.COc1cc2c(Nc3c(Cl)cc(I)c4c3OCO4)ncnc2cc1OCCCN1CCN(C)C(=O)C1 | COc1cc2c(Nc3c(Cl)cc(C#CCC(C)OC)c4c3OCO4)ncnc2cc1OCCCN1CCN(C)C(=O)C1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I | C(C)(=O)OCC | C-C Coupling | Sonogashira alkyne_aryl halide | 4fe05dd9f4e06ca437f6fd540183d70cbf88cbb037b34a93217c201e7139cd32 | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | O=C1CN(CCCOc2ccc3c(Nc4cccc5c4OCO5)ncnc3c2)CCN1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1.[C:9]-[C:10]#[CH;D1;+0:11]>>[C:9]-[C:10]#[C;H0;D2;+0:11]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1 | 73 | [{"value": 73.0, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCC(C)OC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CC(N(CC1)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.0, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCC(C)OC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CC(N(CC1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired":... | null | null | 2 | HOUR | 4-[3-({4-[(5-Chloro-7-iodo-1,3-benzodioxol-4-yl)amino]-6-methoxyquinazolin-7-yl}oxy)propyl]-1-methylpiperazin-2-one (250 mg, 0.40 mmol) and 4-methoxypent-1-yne (120 mg, 1.2 mmol) in ethyl acetate (8 ml) stirred at room temperature, under an atmosphere of nitrogen, and treated with bis(triphenylphosphine)palladium(II) d... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2.c1ccc2ncncc2c1.C1C[NH]CC[NH]1 | HI | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.C(C)(=O)OCC | null | 2 | C#CCC(C)OC.COc1cc2c(Nc3c(Cl)cc(I)c4c3OCO4)ncnc2cc1OCCCN1CCN(C)C(=O)C1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu]I.C(C)(=O)OCC>COc1cc2c(Nc3c(Cl)cc(C#CCC(C)OC)c4c3OCO4)ncnc2cc1OCCCN1CCN(C)C(=O)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a2c30214ee1d4d6aa242cf1f80cba6b9 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1=O.Nc1c(Cl)cc(C#Cc2ccccn2)c2c1OCO2>>COc1cc2c(Nc3c(Cl)cc(C#Cc4ccccn4)c4c3OCO4)ncnc2cc1OCCCN1CCN(C)CC1=O | ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1C(CN(CC1)C)=O.ClC1=C(C2=C(OCO2)C(=C1)C#CC1=NC=CC=C1)N.C[Si](C)(C)[N-][Si](C)(C)C.[Na+]>>ClC1=C(C2=C(OCO2)C(=C1)C#CC1=NC=CC=C1)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1C(CN(CC1)C)=O | Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:31]([O:32][CH2:33][CH2:34][CH2:35][N:36]3[CH2:37][CH2:38][N:39]([CH3:40])[CH2:41][C:42]3=[O:43])[cH:30][c:29]2[n:28][cH:27][n:26]1.[NH2:7][c:8]1[c:9]([Cl:10])[cH:11][c:12]([C:13]#[C:14][c:15]2[cH:16][cH:17][cH:18][cH:19][n:20]2)[c:21]2[c:22]1[O:23][CH2:24][O:25]2>>[CH3:1][O:2][... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1=O.Nc1c(Cl)cc(C#Cc2ccccn2)c2c1OCO2 | COc1cc2c(Nc3c(Cl)cc(C#Cc4ccccn4)c4c3OCO4)ncnc2cc1OCCCN1CCN(C)CC1=O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1CNCCN1CCCOc1ccc2c(Nc3ccc(C#Cc4ccccn4)c4c3OCO4)ncnc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:9]-[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13] | 81.4 | [{"value": 80.0, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CC1=NC=CC=C1)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1C(CN(CC1)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.4, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CC1=NC=CC=C1)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1C(CN(CC1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_d... | null | null | null | null | This was prepared by the method described in example 4 but using 1-{3-[(4-chloro-6-methoxyquinazolin-7-yl)oxy]propyl}-4-methylpiperazin-2-one (137 mg, 0.37 mmol), 5-chloro-7-(pyridin-2-ylethynyl)-1,3-benzodioxol-4-amine (113 mg, 0.41 mmol) and sodium bis(trimethylsilyl)amide (1.0M in THF, 0.8 ml) in DMF (2 ml). The cru... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccncc1.c1ccc2c(c1)OCO2.c1ccc2ncncc2c1.C1C[NH]CC[NH]1 | HCl | CN(C)C=O | null | null | COc1cc2c(Cl)ncnc2cc1OCCCN1CCN(C)CC1=O.Nc1c(Cl)cc(C#Cc2ccccn2)c2c1OCO2>CN(C)C=O>COc1cc2c(Nc3c(Cl)cc(C#Cc4ccccn4)c4c3OCO4)ncnc2cc1OCCCN1CCN(C)CC1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a4998f02435349f59d1147a68dc10e89 | C#CCNC(=O)N(C)C.COc1cc2c(Nc3c(Cl)cc(I)c4c3OCO4)ncnc2cc1OCCCN1C[C@@H](C)O[C@@H](C)C1>>COc1cc2c(Nc3c(Cl)cc(C#CCNC(=O)N(C)C)c4c3OCO4)ncnc2cc1OCCCN1C[C@@H](C)O[C@@H](C)C1 | ClC1=C(C2=C(OCO2)C(=C1)I)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1C[C@H](O[C@H](C1)C)C.CN(C(=O)NCC#C)C.CN(C)C=O>>ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1C[C@H](O[C@H](C1)C)C)C#CCNC(N(C)C)=O | [CH:13]#[C:14][CH2:15][NH:16][C:17](=[O:18])[N:19]([CH3:20])[CH3:21].I[c:12]1[cH:11][c:9]([Cl:10])[c:8]([NH:7][c:6]2[c:5]3[cH:4][c:3]([O:2][CH3:1])[c:32]([O:33][CH2:34][CH2:35][CH2:36][N:37]4[CH2:38][C@@H:39]([CH3:40])[O:41][C@@H:42]([CH3:43])[CH2:44]4)[cH:31][c:30]3[n:29][cH:28][n:27]2)[c:23]2[c:22]1[O:26][CH2:25][O:2... | C#CCNC(=O)N(C)C.COc1cc2c(Nc3c(Cl)cc(I)c4c3OCO4)ncnc2cc1OCCCN1C[C@@H](C)O[C@@H](C)C1 | COc1cc2c(Nc3c(Cl)cc(C#CCNC(=O)N(C)C)c4c3OCO4)ncnc2cc1OCCCN1C[C@@H](C)O[C@@H](C)C1 | null | [Cu]I.Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | C(C)(=O)OCC | C-C Coupling | Sonogashira alkyne_aryl halide | 4fe05dd9f4e06ca437f6fd540183d70cbf88cbb037b34a93217c201e7139cd32 | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1cc(Nc2ncnc3cc(OCCCN4CCOCC4)ccc23)c2c(c1)OCO2 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1.[C:9]-[C:10]#[CH;D1;+0:11]>>[C:9]-[C:10]#[C;H0;D2;+0:11]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1 | 85 | [{"value": 85.0, "product": "ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1C[C@H](O[C@H](C1)C)C)C#CCNC(N(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.4, "product": "ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1C[C@H](O[C@H](C1)C)C)C#CCNC(N(C)C)=O", "details": "CALCULATEDPERCENTY... | null | null | 1 | HOUR | N-(5-Chloro-7-iodo-1,3-benzodioxol-4-yl)-7-[3-(cis-2,6-dimethylmorpholin-4-yl)propoxy]-6-methoxyquinazolin-4-amine (250 mg, 0.40 mmol) and N,N-dimethyl-N′-prop-2-yn-1-ylurea (100 mg, 0.79 mmol) in ethyl acetate (8 ml) stirred at room temperature, under an atmosphere of nitrogen, and treated with bis(triphenylphosphine)... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2.c1ccc2ncncc2c1.C1COCC[NH]1 | HI | [Cu]I.Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.C(C)(=O)OCC | null | 1 | C#CCNC(=O)N(C)C.COc1cc2c(Nc3c(Cl)cc(I)c4c3OCO4)ncnc2cc1OCCCN1C[C@@H](C)O[C@@H](C)C1>[Cu]I.Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.C(C)(=O)OCC>COc1cc2c(Nc3c(Cl)cc(C#CCNC(=O)N(C)C)c4c3OCO4)ncnc2cc1OCCCN1C[C@@H](C)O[C@@H](C)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7128598e468640a8bbab34775df2d5e7 | COCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Oc3c(F)c(F)c(F)c(F)c3F)ncnc2cc1OCCN1CCOCC1>>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCN4CCOCC4)c(OC)cc23)c2c1OCO2 | [Cl-].[NH4+].C[Si](C)(C)[N-][Si](C)(C)C.[Na+].O1CCCC1.COC=1C=C2C(=NC=NC2=CC1OCCN1CCOCC1)OC1=C(C(=C(C(=C1F)F)F)F)F.ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)N>>ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCN1CCOCC1 | [CH3:1][O:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][c:8]([Cl:9])[c:10]([NH2:11])[c:33]2[c:34]1[O:35][CH2:36][O:37]2.Fc1c(F)c(F)c(O[c:12]2[n:13][cH:14][n:15][c:16]3[cH:17][c:18]([O:19][CH2:20][CH2:21][N:22]4[CH2:23][CH2:24][O:25][CH2:26][CH2:27]4)[c:28]([O:29][CH3:30])[cH:31][c:32]23)c(F)c1F>>[CH3:1][O:2][CH2:3][C:4]#[C:5][c:6]1... | COCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Oc3c(F)c(F)c(F)c(F)c3F)ncnc2cc1OCCN1CCOCC1 | COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCN4CCOCC4)c(OC)cc23)c2c1OCO2 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Displacement of ethoxy group by primary amine | 2dede08b81b2d73e5df0a1a81ae338f4d219d89005aab0f235b45b0587f7071c | c75115d0fac1383e820930b1a212a32fb85a64fcc190d377ed77a74cda410dbf | c1cc(Nc2ncnc3cc(OCCN4CCOCC4)ccc23)c2c(c1)OCO2 | F-c1:c(-F):c(-F):c(-O-[c;H0;D3;+0:1]2:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:2:[c:8]):c(-F):c:1-F.[#8:9]-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:9]-[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13] | 8 | [{"value": 8.0, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCN1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 7.4, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCN1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of sodium bis(trimethylsilyl)amide (1.63 ml) in tetrahydrofuran (1.0M, 1.63 mmol) was added dropwise to an ice-cold solution of 6-methoxy-7-(2-morpholin-4-ylethoxy)-4-(pentafluorophenoxy)quinazoline (0.35 g, 0.74 mmol) and 5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-amine (0.213 g, 0.89 mmol) in d... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Ether.Primary amine | Secondary amine | c1ccccc1.c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1COCC[NH]1.c1ccc2c(c1)OCO2 | HF | CN(C=O)C | null | null | COCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Oc3c(F)c(F)c(F)c(F)c3F)ncnc2cc1OCCN1CCOCC1>CN(C=O)C>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCN4CCOCC4)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8ad3d9a80e0243b48b38504a2db8568c | COc1cc2c(Cl)ncnc2cc1O.ClCCCCBr>>COc1cc2c(Cl)ncnc2cc1OCCCCCl | ClC1=NC=NC2=CC(=C(C=C12)OC)O.BrCCCCCl.C([O-])([O-])=O.[K+].[K+]>>ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCCCl | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:7])[n:8][cH:9][n:10][c:11]2[cH:12][c:13]1[OH:14].Br[CH2:15][CH2:16][CH2:17][CH2:18][Cl:19]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:7])[n:8][cH:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][CH2:16][CH2:17][CH2:18][Cl:19] | COc1cc2c(Cl)ncnc2cc1O.ClCCCCBr | COc1cc2c(Cl)ncnc2cc1OCCCCCl | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc2ncncc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7;a:4]:[c:5]:[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[#7;a:4]:[c:5]:[c:6]:[c:7](-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:9] | 47 | [{"value": 47.0, "product": "ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCCCl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.4, "product": "ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCCCl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of 4-chloro-6-methoxyquinazolin-7-ol (0.6 g, 2.86 mmol), 1 bromo 4 chlorobutane (0.63 g, 3.7 mmol), potassium carbonate (1.19 g, 8.6 mmol) and dimethylformamide (10 ml) were heated to 95 C for 1.5 hours. The excess potassium carbonate was filtered off and the reaction evaporated under reduced pressure. The... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2ncncc2c1 | HBr | CN(C=O)C | null | null | COc1cc2c(Cl)ncnc2cc1O.ClCCCCBr>CN(C=O)C>COc1cc2c(Cl)ncnc2cc1OCCCCCl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7be5ce8be65f47ca928b7c5a651b2dba | COCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCCCl>>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCCl)c(OC)cc23)c2c1OCO2 | [Cl-].[NH4+].C[Si](C)(C)[N-][Si](C)(C)C.[Na+].O1CCCC1.ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCCCl.ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)N>>ClCCCCOC1=C(C=C2C(=NC=NC2=C1)NC1=C(C=C(C=2OCOC21)C#CCOC)Cl)OC | [CH3:1][O:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][c:8]([Cl:9])[c:10]([NH2:11])[c:30]2[c:31]1[O:32][CH2:33][O:34]2.Cl[c:12]1[n:13][cH:14][n:15][c:16]2[cH:17][c:18]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][Cl:24])[c:25]([O:26][CH3:27])[cH:28][c:29]12>>[CH3:1][O:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][c:8]([Cl:9])[c:10]([NH:11][c:12]2[n:... | COCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCCCl | COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCCl)c(OC)cc23)c2c1OCO2 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ncnc3ccccc23)c2c(c1)OCO2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:9]-[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13] | 73.5 | [{"value": 73.0, "product": "ClCCCCOC1=C(C=C2C(=NC=NC2=C1)NC1=C(C=C(C=2OCOC21)C#CCOC)Cl)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.5, "product": "ClCCCCOC1=C(C=C2C(=NC=NC2=C1)NC1=C(C=C(C=2OCOC21)C#CCOC)Cl)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of sodium bis(trimethylsilyl)amide (2.66 ml) in tetrahydrofuran (1.0M, 2.66 mmol) was added dropwise to an ice-cold solution of 4-chloro-7-(4-chlorobutoxy)-6-methoxyquinazoline (0.4 g, 1.33 mmol) and 5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-amine (0.35 g, 1.47 mmol) in dimethylformamide (4 ml).... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccc2c(c1)OCO2 | HCl | CN(C=O)C | null | null | COCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCCCl>CN(C=O)C>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCCl)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2c20b06201a341cb95c1c560d9998edb | CC(=O)N1CCNCC1.COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCCl)c(OC)cc23)c2c1OCO2>>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCN4CCN(C(C)=O)CC4)c(OC)cc23)c2c1OCO2 | ClCCCCOC1=C(C=C2C(=NC=NC2=C1)NC1=C(C=C(C=2OCOC21)C#CCOC)Cl)OC.C(C)N(CC)CC.C(C)(=O)N1CCNCC1.COC(C)O>>C(C)(=O)N1CCN(CC1)CCCCOC1=C(C=C2C(=NC=NC2=C1)NC1=C(C=C(C=2OCOC21)C#CCOC)Cl)OC | [NH:24]1[CH2:25][CH2:26][N:27]([C:28]([CH3:29])=[O:30])[CH2:31][CH2:32]1.Cl[CH2:23][CH2:22][CH2:21][CH2:20][O:19][c:18]1[cH:17][c:16]2[n:15][cH:14][n:13][c:12]([NH:11][c:10]3[c:8]([Cl:9])[cH:7][c:6]([C:5]#[C:4][CH2:3][O:2][CH3:1])[c:39]4[c:38]3[O:42][CH2:41][O:40]4)[c:37]2[cH:36][c:33]1[O:34][CH3:35]>>[CH3:1][O:2][CH2:... | CC(=O)N1CCNCC1.COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCCl)c(OC)cc23)c2c1OCO2 | COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCN4CCN(C(C)=O)CC4)c(OC)cc23)c2c1OCO2 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc(Nc2ncnc3cc(OCCCCN4CCNCC4)ccc23)c2c(c1)OCO2 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | 17.2 | [{"value": 17.0, "product": "C(C)(=O)N1CCN(CC1)CCCCOC1=C(C=C2C(=NC=NC2=C1)NC1=C(C=C(C=2OCOC21)C#CCOC)Cl)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 17.2, "product": "C(C)(=O)N1CCN(CC1)CCCCOC1=C(C=C2C(=NC=NC2=C1)NC1=C(C=C(C=2OCOC21)C#CCOC)Cl)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": fal... | null | null | 7 | HOUR | A mixture of 7-(4-chlorobutoxy)-N-[5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-yl]-6-methoxyquinazolin-4-amine (0.23 g, 0.4 mmol), triethylamine (0.22 ml, 1.6 mmol), N-acetyl piperazine (0.205 g, 1.6 mmol) in 2 methoxyethanol (2 ml) was heated to 80 C for 12 hours and then at 100 C for 7 hours. The solvent w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccc2ncncc2c1.C1C[NH]CC[NH]1.c1ccc2c(c1)OCO2 | HCl | null | null | 7 | CC(=O)N1CCNCC1.COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCCl)c(OC)cc23)c2c1OCO2>>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCN4CCN(C(C)=O)CC4)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7e87489c86c8491dbb4136f96c54b9cd | COc1cc2c(Cl)ncnc2cc1O.ClCCBr>>COc1cc2c(Cl)ncnc2cc1OCCCl | ClC1=NC=NC2=CC(=C(C=C12)OC)O.BrCCCl.C([O-])([O-])=O.[K+].[K+]>>ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCl | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:7])[n:8][cH:9][n:10][c:11]2[cH:12][c:13]1[OH:14].Br[CH2:15][CH2:16][Cl:17]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([Cl:7])[n:8][cH:9][n:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][CH2:16][Cl:17] | COc1cc2c(Cl)ncnc2cc1O.ClCCBr | COc1cc2c(Cl)ncnc2cc1OCCCl | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc2ncncc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[Cl;D1;H0:3].[#7;a:4]:[c:5]:[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[#7;a:4]:[c:5]:[c:6]:[c:7](-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[C:2]-[Cl;D1;H0:3]):[c:9] | 57 | [{"value": 57.0, "product": "ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.2, "product": "ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of 4-chloro-6-methoxyquinazolin-7-ol (1.2 g, 5.8 mmol), 1 bromo 2 chloroethane (5.69 ml, 6.8 mmol), potassium carbonate (2.36 g, 17.4 mmol) and dimethylformamide (15 ml) were heated to 90 C for 1.5 hours. The excess potassium carbonate was filtered off and the reaction evaporated under reduced pressure. Th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2ncncc2c1 | HBr | CN(C=O)C | null | null | COc1cc2c(Cl)ncnc2cc1O.ClCCBr>CN(C=O)C>COc1cc2c(Cl)ncnc2cc1OCCCl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c68572d711c844ab8834df9b2d660fa7 | C1CCOC1.COCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCl.[NH4+]>>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCNCCCO)c(OC)cc23)c2c1OCO2 | [Cl-].[NH4+].C[Si](C)(C)[N-][Si](C)(C)C.[Na+].O1CCCC1.ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCl.ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)N>>ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCNCCCO | C1[CH2:23][CH2:24][CH2:25][O:26]1.[CH3:1][O:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][c:8]([Cl:9])[c:10]([NH2:11])[c:32]2[c:33]1[O:34][CH2:35][O:36]2.Cl[c:12]1[n:13][cH:14][n:15][c:16]2[cH:17][c:18]([O:19][CH2:20][CH2:21]Cl)[c:27]([O:28][CH3:29])[cH:30][c:31]12.[NH4+:22]>>[CH3:1][O:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][c:8]([Cl:9])[... | C1CCOC1.COCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCl.[NH4+] | COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCNCCCO)c(OC)cc23)c2c1OCO2 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 973df3fb102481b8c95351ef45fd0a51c91f4a025c526ec65a5bfc46adeeedcd | 17772e56b609872eda6e86f97c06406783a5d7602192eceaede2517053039cb0 | c1cc(Nc2ncnc3ccccc23)c2c(c1)OCO2 | C1-[CH2;D2;+0:1]-[C:2]-[C:3]-[O;H0;D2;+0:4]-1.Cl-[CH2;D2;+0:5]-[C:6]-[#8:7].Cl-[c;H0;D3;+0:8]1:[#7;a:9]:[c:10]:[#7;a:11]:[c:12](:[c:13]):[c:14]:1:[c:15].[#8:16]-[c:17]:[c:18](-[NH2;D1;+0:19]):[c:20].[NH4+;D0:21]>>[#8:7]-[C:6]-[CH2;D2;+0:5]-[NH;D2;+0:21]-[CH2;D2;+0:1]-[C:2]-[C:3]-[OH;D1;+0:4].[#8:16]-[c:17]:[c:18](-[NH;... | null | [] | null | null | null | null | A solution of sodium bis(trimethylsilyl)amide (5.6 ml) in tetrahydrofuran (1.0M, 5.6 mmol) was added dropwise to an ice-cold solution of 4-chloro-7-(2-chloroethoxy)-6-methoxyquinazoline (0.7 g, 2.6 mmol) and 5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-amine (0.675 g, 2.8 mmol) in dimethylformamide (8 ml). Th... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary halide.Ether.Primary amine | Primary alcohol.Secondary amine.Secondary amine | C1CCOC1.c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccc2c(c1)OCO2 | HCl | CN(C=O)C | null | null | C1CCOC1.COCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCl.[NH4+]>CN(C=O)C>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCNCCCO)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e7ff0015a9634254bfe73bb5c5b0b878 | CN1CCNCC1.COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCl)c(OC)cc23)c2c1OCO2>>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCN4CCN(C)CC4)c(OC)cc23)c2c1OCO2 | ClCCOC1=C(C=C2C(=NC=NC2=C1)NC1=C(C=C(C=2OCOC21)C#CCOC)Cl)OC.CN1CCNCC1>>ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCN1CCN(CC1)C | [NH:22]1[CH2:23][CH2:24][N:25]([CH3:26])[CH2:27][CH2:28]1.Cl[CH2:21][CH2:20][O:19][c:18]1[cH:17][c:16]2[n:15][cH:14][n:13][c:12]([NH:11][c:10]3[c:8]([Cl:9])[cH:7][c:6]([C:5]#[C:4][CH2:3][O:2][CH3:1])[c:35]4[c:34]3[O:38][CH2:37][O:36]4)[c:33]2[cH:32][c:29]1[O:30][CH3:31]>>[CH3:1][O:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][c:8](... | CN1CCNCC1.COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCl)c(OC)cc23)c2c1OCO2 | COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCN4CCN(C)CC4)c(OC)cc23)c2c1OCO2 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc(Nc2ncnc3cc(OCCN4CCNCC4)ccc23)c2c(c1)OCO2 | Cl-[CH2;D2;+0:1]-[C:2]-[#8:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | 17 | [{"value": 17.0, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCN1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 7-(2-Chloroethoxy)-N-[5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-yl]-6-methoxyquinazolin-4-amine (0.2 g, 0.4 mmol) was dissolved in 1-methylpiperazine (4 ml) and heated at 50 C for 12 hours. The solvent was evaporated under reduced pressure and the residue purified by flash chromatography on alumina eluting... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccc2ncncc2c1.C1C[NH]CC[NH]1.c1ccc2c(c1)OCO2 | HCl | null | null | null | CN1CCNCC1.COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCl)c(OC)cc23)c2c1OCO2>>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCN4CCN(C)CC4)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a2ea710336cc4b5e82dfc827cf25ab1c | COCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2ncnc(Cl)c2cc1OC>>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OC)c(OC)cc23)c2c1OCO2 | [Cl-].[NH4+].C[Si](C)(C)[N-][Si](C)(C)C.[Na+].O1CCCC1.ClC1=NC=NC2=CC(=C(C=C12)OC)OC.ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)N>>ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OC | [CH3:1][O:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][c:8]([Cl:9])[c:10]([NH2:11])[c:26]2[c:27]1[O:28][CH2:29][O:30]2.Cl[c:12]1[n:13][cH:14][n:15][c:16]2[cH:17][c:18]([O:19][CH3:20])[c:21]([O:22][CH3:23])[cH:24][c:25]12>>[CH3:1][O:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][c:8]([Cl:9])[c:10]([NH:11][c:12]2[n:13][cH:14][n:15][c:16]3[cH:17][... | COCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2ncnc(Cl)c2cc1OC | COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OC)c(OC)cc23)c2c1OCO2 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ncnc3ccccc23)c2c(c1)OCO2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:9]-[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13] | 60 | [{"value": 60.0, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.4, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of sodium bis(trimethylsilyl)amide (1.5 ml) in tetrahydrofuran (1.0M, 1.5 mmol) was added dropwise to an ice-cold solution of 4-chloro-6,7-dimethoxyquinazoline (0.15 g, 0.7 mmol) and 5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-amine (0.176 g, 0.7 mmol) in dimethylformamide (4 ml). The mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccc2c(c1)OCO2 | HCl | CN(C=O)C | null | null | COCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2ncnc(Cl)c2cc1OC>CN(C=O)C>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OC)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-abd2f4179249463d84bddcf087027373 | CCOC(C)=O.COc1cc2c(Nc3c(Cl)cc(I)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1>>COc1cc2c(Nc3c(Cl)cc(C#CCO)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | ClC1=C(C2=C(OCO2)C(=C1)I)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1.C(C)(C)NC(C)C.C(C)(=O)OCC>>ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1)C#CCO | C[CH2:15]O[C:13]([CH3:14])=[O:16].I[c:12]1[cH:11][c:9]([Cl:10])[c:8]([NH:7][c:6]2[c:5]3[cH:4][c:3]([O:2][CH3:1])[c:27]([O:28][CH2:29][CH2:30][CH2:31][N:32]4[CH2:33][CH2:34][O:35][CH2:36][CH2:37]4)[cH:26][c:25]3[n:24][cH:23][n:22]2)[c:18]2[c:17]1[O:21][CH2:20][O:19]2>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][c:8]3[c:9... | CCOC(C)=O.COc1cc2c(Nc3c(Cl)cc(I)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | COc1cc2c(Nc3c(Cl)cc(C#CCO)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | null | [Cu]I.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl | null | Heteroatom Alkylation and Arylation | OtherReaction | 510b24b9251fb7537b22208492e69eb348ef95d3150dca331f76fc17d57d025c | 7d68760c243837318f86bd692eb74f60749949a7b0ba0646da27e5507dfa9ce6 | c1cc(Nc2ncnc3cc(OCCCN4CCOCC4)ccc23)c2c(c1)OCO2 | C-[CH2;D2;+0:1]-O-[C;H0;D3;+0:2](-[CH3;D1;+0:3])=[O;H0;D1;+0:4].I-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]1:[c:9]-[#8:10]-[C:11]-[#8:12]-1>>[OH;D1;+0:4]-[CH2;D2;+0:1]-[C;H0;D2;+0:3]#[C;H0;D2;+0:2]-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]1:[c:9]-[#8:10]-[C:11]-[#8:12]-1 | 51 | [{"value": 51.0, "product": "ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1)C#CCO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of N-(5-chloro-7-iodo-1,3-benzodioxol-4-yl)-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazolin-4-amine (0.35 g, 0.59 mmol) propargyl alcohol (0.075 ml, 1.3 mmol) and diisopropylamine (0.18 ml, 1.3 mmol) in ethyl acetate (10 ml) was cooled to −20 C under a nitrogen atmosphere. To this was added copper (I) iodide... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester | Primary alcohol.Alkyne | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2.c1ccc2ncncc2c1.C1COCC[NH]1 | HI | [Cu]I.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl | null | 8 | CCOC(C)=O.COc1cc2c(Nc3c(Cl)cc(I)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1>[Cu]I.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl>COc1cc2c(Nc3c(Cl)cc(C#CCO)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-831c118a627246c8bcd8b1ee325f0ad3 | C#Cc1ccccc1.COc1cc2c(Nc3c(Cl)cc(I)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1>>COc1cc2c(Nc3c(Cl)cc(C#Cc4ccccc4)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | ClC1=C(C2=C(OCO2)C(=C1)I)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1.C1(=CC=CC=C1)C#C.C(C)(C)NC(C)C>>ClC1=C(C2=C(OCO2)C(=C1)C#CC1=CC=CC=C1)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1 | [CH:13]#[C:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1.I[c:12]1[cH:11][c:9]([Cl:10])[c:8]([NH:7][c:6]2[c:5]3[cH:4][c:3]([O:2][CH3:1])[c:31]([O:32][CH2:33][CH2:34][CH2:35][N:36]4[CH2:37][CH2:38][O:39][CH2:40][CH2:41]4)[cH:30][c:29]3[n:28][cH:27][n:26]2)[c:22]2[c:21]1[O:25][CH2:24][O:23]2>>[CH3:1][O:2][c:3]1[cH:4][c:5... | C#Cc1ccccc1.COc1cc2c(Nc3c(Cl)cc(I)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | COc1cc2c(Nc3c(Cl)cc(C#Cc4ccccc4)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | null | [Cu]I.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl | C(C)(=O)OCC | C-C Coupling | Sonogashira alkyne_aryl halide | 4fe05dd9f4e06ca437f6fd540183d70cbf88cbb037b34a93217c201e7139cd32 | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | C(#Cc1ccc(Nc2ncnc3cc(OCCCN4CCOCC4)ccc23)c2c1OCO2)c1ccccc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1.[CH;D1;+0:9]#[C:10]-[c:11]>>[c:11]-[C:10]#[C;H0;D2;+0:9]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1 | 66.1 | [{"value": 66.0, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CC1=CC=CC=C1)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.1, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CC1=CC=CC=C1)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | null | null | 8 | HOUR | A mixture of N-(5-chloro-7-iodo-1,3-benzodioxol-4-yl)-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazolin-4-amine (0.17 g, 0.285 mmol), phenyl acetylene (0.07 ml, 0.63 mmol) and diisopropylamine (0.088 ml, 0.63 mmol) in ethyl acetate (4 ml) was cooled to −20 C under a nitrogen atmosphere. To this was added copper (I) iodid... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | c1ccccc1.c1ccc2c(c1)OCO2.c1ccc2ncncc2c1.C1COCC[NH]1 | HI | [Cu]I.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.C(C)(=O)OCC | null | 8 | C#Cc1ccccc1.COc1cc2c(Nc3c(Cl)cc(I)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1>[Cu]I.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.C(C)(=O)OCC>COc1cc2c(Nc3c(Cl)cc(C#Cc4ccccc4)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-42ebd4f6cf8f40cb83628d45d3eba932 | C#C[Si](C)(C)C.Nc1c(Cl)cc(I)c2c1OCO2>>C[Si](C)(C)C#Cc1cc(Cl)c(N)c2c1OCO2 | C(C)(C)NC(C)C.ClC1=C(C2=C(OCO2)C(=C1)I)N.C[Si](C)(C)C#C>>ClC1=C(C2=C(OCO2)C(=C1)C#C[Si](C)(C)C)N | [CH3:1][Si:2]([CH3:3])([CH3:4])[C:5]#[CH:6].I[c:7]1[cH:8][c:9]([Cl:10])[c:11]([NH2:12])[c:13]2[c:14]1[O:15][CH2:16][O:17]2>>[CH3:1][Si:2]([CH3:3])([CH3:4])[C:5]#[C:6][c:7]1[cH:8][c:9]([Cl:10])[c:11]([NH2:12])[c:13]2[c:14]1[O:15][CH2:16][O:17]2 | C#C[Si](C)(C)C.Nc1c(Cl)cc(I)c2c1OCO2 | C[Si](C)(C)C#Cc1cc(Cl)c(N)c2c1OCO2 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | C(C)(=O)OCC | C-C Coupling | Sonogashira alkyne_aryl halide | 4fe05dd9f4e06ca437f6fd540183d70cbf88cbb037b34a93217c201e7139cd32 | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccc2c(c1)OCO2 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1.[C;D1;H3:9]-[#14:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[C:13]#[CH;D1;+0:14]>>[C;D1;H3:9]-[#14:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[C:13]#[C;H0;D2;+0:14]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1 | null | [] | -20 | CELSIUS | 4 | HOUR | Bis(triphenylphosphine)palladium(II) chloride (0.283 g), cuprous iodide (0.115 g) and diisopropylamine (0.57 ml) were added to a stirred solution of 5-chloro-7-iodo-1,3-benzodioxol-4-amine (0.600 g) and trimethylsilylacetylene (0.57 ml) in ethyl acetate (10 ml) cooled to −20° C. under a nitrogen atmosphere. The mixture... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | HI | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.C(C)(=O)OCC | -20 | 4 | C#C[Si](C)(C)C.Nc1c(Cl)cc(I)c2c1OCO2>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.C(C)(=O)OCC>C[Si](C)(C)C#Cc1cc(Cl)c(N)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a63e5ccd836d4687a6eccc8a3bc7a955 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.C[Si](C)(C)C#Cc1cc(Cl)c(N)c2c1OCO2>>C#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCOCC4)c(OC)cc23)c2c1OCO2 | C[Si](C)(C)[N-][Si](C)(C)C.[Na+].O1CCCC1.ClC1=C(C2=C(OCO2)C(=C1)C#C[Si](C)(C)C)N.ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1>>ClC1=C(C2=C(OCO2)C(=C1)C#C)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1 | Cl[c:9]1[n:10][cH:11][n:12][c:13]2[cH:14][c:15]([O:16][CH2:17][CH2:18][CH2:19][N:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)[c:26]([O:27][CH3:28])[cH:29][c:30]12.C[Si](C)(C)[C:1]#[C:2][c:3]1[cH:4][c:5]([Cl:6])[c:7]([NH2:8])[c:31]2[c:32]1[O:33][CH2:34][O:35]2>>[CH:1]#[C:2][c:3]1[cH:4][c:5]([Cl:6])[c:7]([NH:8][c:9]2[n:1... | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.C[Si](C)(C)C#Cc1cc(Cl)c(N)c2c1OCO2 | C#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCOCC4)c(OC)cc23)c2c1OCO2 | null | null | [Cl-].[NH4+].CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 23f2cf31fe2b12633627977b4ad95fa803ea6430bf1086f434c848e53d605677 | 521ea30c7bc250dd6f5abcf4b27d24817aae41cc52e7ce3622397d83ac2906ea | c1cc(Nc2ncnc3cc(OCCCN4CCOCC4)ccc23)c2c(c1)OCO2 | C-[Si](-C)(-C)-[C;H0;D2;+0:1]#[C:2]-[c:3].[#8:4]-[c:5]:[c:6](-[NH2;D1;+0:7]):[c:8].Cl-[c;H0;D3;+0:9]1:[#7;a:10]:[c:11]:[#7;a:12]:[c:13](:[c:14]):[c:15]:1:[c:16]>>[#8:4]-[c:5]:[c:6](-[NH;D2;+0:7]-[c;H0;D3;+0:9]1:[#7;a:10]:[c:11]:[#7;a:12]:[c:13](:[c:14]):[c:15]:1:[c:16]):[c:8].[CH;D1;+0:1]#[C:2]-[c:3] | 58.3 | [{"value": 58.3, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#C)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | A solution of sodium bis(trimethylsilyl)amide (0.91 ml) in tetrahydrofuran (1.0M, 0.91 mmol) was added over 5 min. to a stirred mixture of {5-chloro-7-[(trimethylsilyl)ethynyl]-1,3-benzodioxol-4-yl}amine (0.122 g) and 4-chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline (0.140 g) in DMF (4 ml) cooled to 0° C. unde... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine.Alkyne.Silyl protective group | Secondary amine.Alkyne | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1COCC[NH]1.c1ccc2c(c1)OCO2 | HCl | [Cl-].[NH4+].CN(C)C=O | 0 | 1 | COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1.C[Si](C)(C)C#Cc1cc(Cl)c(N)c2c1OCO2>[Cl-].[NH4+].CN(C)C=O>C#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCOCC4)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d394345ceffc4175918a2082bca6edb8 | CN1CCNCC1=O.COc1cc2c(Nc3c(Cl)cc(C#CCOC(C)C)c4c3OCO4)ncnc2cc1OCCCCl>>COc1cc2c(Nc3c(Cl)cc(C#CCOC(C)C)c4c3OCO4)ncnc2cc1OCCCN1CCN(C)C(=O)C1 | ClC1=C(C2=C(OCO2)C(=C1)C#CCOC(C)C)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCCl.C(C)N(CC)CC.CN1C(CNCC1)=O>>ClC1=C(C2=C(OCO2)C(=C1)C#CCOC(C)C)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CC(N(CC1)C)=O | [NH:35]1[CH2:36][CH2:37][N:38]([CH3:39])[C:40](=[O:41])[CH2:42]1.Cl[CH2:34][CH2:33][CH2:32][O:31][c:30]1[c:3]([O:2][CH3:1])[cH:4][c:5]2[c:6]([NH:7][c:8]3[c:9]([Cl:10])[cH:11][c:12]([C:13]#[C:14][CH2:15][O:16][CH:17]([CH3:18])[CH3:19])[c:20]4[c:21]3[O:22][CH2:23][O:24]4)[n:25][cH:26][n:27][c:28]2[cH:29]1>>[CH3:1][O:2][c... | CN1CCNCC1=O.COc1cc2c(Nc3c(Cl)cc(C#CCOC(C)C)c4c3OCO4)ncnc2cc1OCCCCl | COc1cc2c(Nc3c(Cl)cc(C#CCOC(C)C)c4c3OCO4)ncnc2cc1OCCCN1CCN(C)C(=O)C1 | null | null | COCCO | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1CN(CCCOc2ccc3c(Nc4cccc5c4OCO5)ncnc3c2)CCN1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1=[O;D1;H0:11]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5](-[C;D1;H3:4])-[C:10](=[O;D1;H0:11])-[C:9]-1 | 51 | [{"value": 51.0, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCOC(C)C)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CC(N(CC1)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.3, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCOC(C)C)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CC(N(CC1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired":... | null | null | 7 | HOUR | A mixture of N-[5-chloro-7-(3-isopropoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-yl]-7-(3-chloropropoxy)-6-methoxyquinazolin-4-amine (0.22 g, 0.43 mmol), triethylamine (0.29 ml, 2.13 mmol), 1-methylpiperazin-2-one (0.24 g, 2.13 mmol) in 2-methoxyethanol (3 ml) was heated to 80 C for 12 hours and then at 100 C for 7 hours. The... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccc2c(c1)OCO2.c1ccc2ncncc2c1.C1C[NH]CC[NH]1 | HCl | COCCO | null | 7 | CN1CCNCC1=O.COc1cc2c(Nc3c(Cl)cc(C#CCOC(C)C)c4c3OCO4)ncnc2cc1OCCCCl>COCCO>COc1cc2c(Nc3c(Cl)cc(C#CCOC(C)C)c4c3OCO4)ncnc2cc1OCCCN1CCN(C)C(=O)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e8715fbe9663403b87216859031940bb | Cc1ccccc1S(=O)(=O)Cl.c1cn[nH]c1>>Cc1ccc(S(=O)(=O)n2cccn2)cc1 | N1N=CC=C1.ClCCl.C=1(C(=CC=CC1)S(=O)(=O)Cl)C>>CC1=CC=C(C=C1)S(=O)(=O)N1N=CC=C1 | Cl[S:6]([c:5]1[c:2]([CH3:1])[cH:3][cH:4][cH:15][cH:14]1)(=[O:7])=[O:8].[nH:9]1[cH:10][cH:11][cH:12][n:13]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[n:9]2[cH:10][cH:11][cH:12][n:13]2)[cH:14][cH:15]1 | Cc1ccccc1S(=O)(=O)Cl.c1cn[nH]c1 | Cc1ccc(S(=O)(=O)n2cccn2)cc1 | null | null | N1=CC=CC=C1 | Miscellaneous | OtherReaction | 09172568984cc12ebc6aa2cc46f577583dffea6b9039dbb69193dc70a384646d | 7f3e86b6630762f64990327f31f62fdc5c57759ae379b01949b1f753af3f1b5b | O=S(=O)(c1ccccc1)n1cccn1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c;H0;D3;+0:4]1:[c:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:[c:8]:[c;H0;D3;+0:9]:1-[C;D1;H3:10].[#7;a:11]1:[c:12]:[c:13]:[c:14]:[nH;D2;+0:15]:1>>[C;D1;H3:10]-[c;H0;D3;+0:9]1:[c:8]:[cH;D2;+0:7]:[c;H0;D3;+0:4](-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[n;H0;D3;+0:15]2:[#7;a:11]:[c:12]:... | 76 | [{"value": 76.0, "product": "CC1=CC=C(C=C1)S(=O)(=O)N1N=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of pyrazole (2 g, 29.0 mmol), dichloromethane (20 ml) and pyridine (5 ml) was added 4 toluene sulphonyl chloride (6.89 g, 36 mmol) and the reaction mixture stirred at ambient temperature for 1 hour. The reaction mixture was partitioned between dichlormethane and an aqueous solution of sodium bicarbonate. ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Tosylate | c1ccccc1.c1cn[nH]c1 | c1ccccc1.c1cn[nH]c1 | c1ccccc1.c1cn[nH]c1 | HCl | N1=CC=CC=C1 | null | 1 | Cc1ccccc1S(=O)(=O)Cl.c1cn[nH]c1>N1=CC=CC=C1>Cc1ccc(S(=O)(=O)n2cccn2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0045a542e99440d9bdd0be7f9c396df2 | Cc1ccc(S(=O)(=O)n2cccn2)cc1.II>>Cc1ccc(S(=O)(=O)n2nccc2I)cc1 | C(C)(C)(C)[Li].CCCCC.CC1=CC=C(C=C1)S(=O)(=O)N1N=CC=C1.II.[Cl-].[NH4+]>>IC1=CC=NN1S(=O)(=O)C1=CC=C(C=C1)C | [CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[n:9]2[n:10][cH:11][cH:12][cH:13]2)[cH:15][cH:16]1.I[I:14]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[n:9]2[n:10][cH:11][cH:12][c:13]2[I:14])[cH:15][cH:16]1 | Cc1ccc(S(=O)(=O)n2cccn2)cc1.II | Cc1ccc(S(=O)(=O)n2nccc2I)cc1 | null | null | C1CCOC1 | Functional Group Interconversion | OtherReaction | c863b350bc8d0b26ec5b34300cfa70480d7718c7a9e7b7df2a5a16303c53f073 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | O=S(=O)(c1ccccc1)n1cccn1 | I-[I;H0;D1;+0:1].[#16:2]-[#7;a:3]1:[#7;a:4]:[c:5]:[c:6]:[cH;D2;+0:7]:1>>[#16:2]-[#7;a:3]1:[#7;a:4]:[c:5]:[c:6]:[c;H0;D3;+0:7]:1-[I;H0;D1;+0:1] | 30.6 | [{"value": 30.0, "product": "IC1=CC=NN1S(=O)(=O)C1=CC=C(C=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.6, "product": "IC1=CC=NN1S(=O)(=O)C1=CC=C(C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of 1-[(4-methylphenyl)sulfonyl]-1H-pyrazole (2.0 g, 9.0 mmol) in THF (50 ml) was cooled to −78 C under a nitrogen atmosphere. To this was added tert butyl lithium (5.9 ml) in pentane (1.7M, 10 mmol). After 10 minutes iodine (2.53 g, 10 mmol) in THF (10 ml) was added and the reaction mixture was stirred for a... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1cn[nH]c1 | c1ccn[nH]1 | c1ccccc1.c1ccn[nH]1 | HI | C1CCOC1 | null | 0.5 | Cc1ccc(S(=O)(=O)n2cccn2)cc1.II>C1CCOC1>Cc1ccc(S(=O)(=O)n2nccc2I)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-040cac7a9c584dd08573d99a3cb4cd8a | C#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCOCC4)c(OC)cc23)c2c1OCO2.Cc1ccc(S(=O)(=O)n2nccc2I)cc1>>COc1cc2c(Nc3c(Cl)cc(C#Cc4ccnn4S(=O)(=O)c4ccc(C)cc4)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | ClC1=C(C2=C(OCO2)C(=C1)C#C)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1.IC1=CC=NN1S(=O)(=O)C1=CC=C(C=C1)C.C(C)(C)NC(C)C>>ClC1=C(C2=C(OCO2)C(=C1)C#CC1=CC=NN1S(=O)(=O)C1=CC=C(C=C1)C)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1 | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][c:8]3[c:9]([Cl:10])[cH:11][c:12]([C:13]#[CH:14])[c:30]4[c:31]3[O:32][CH2:33][O:34]4)[n:35][cH:36][n:37][c:38]2[cH:39][c:40]1[O:41][CH2:42][CH2:43][CH2:44][N:45]1[CH2:46][CH2:47][O:48][CH2:49][CH2:50]1.I[c:15]1[cH:16][cH:17][n:18][n:19]1[S:20](=[O:21])(=[O:22])[c:23]1[cH:24][cH... | C#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCOCC4)c(OC)cc23)c2c1OCO2.Cc1ccc(S(=O)(=O)n2nccc2I)cc1 | COc1cc2c(Nc3c(Cl)cc(C#Cc4ccnn4S(=O)(=O)c4ccc(C)cc4)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | null | [Cu]I.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl | C(C)(=O)OCC | C-C Coupling | Sonogashira alkyne_aryl halide | e409f958c2928962905ab902c452f34fe5ffd3d0a23cbb1eb933eff57c4d9f31 | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | O=S(=O)(c1ccccc1)n1nccc1C#Cc1ccc(Nc2ncnc3cc(OCCCN4CCOCC4)ccc23)c2c1OCO2 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[#7;a:5]:1-[#16:6].[CH;D1;+0:7]#[C:8]-[c:9]>>[#16:6]-[#7;a:5]1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[C;H0;D2;+0:7]#[C:8]-[c:9] | 51.3 | [{"value": 51.0, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CC1=CC=NN1S(=O)(=O)C1=CC=C(C=C1)C)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.3, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CC1=CC=NN1S(=O)(=O)C1=CC=C(C=C1)C)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1", "details": "CA... | null | null | 8 | HOUR | A solution of N-(5-chloro-7-ethynyl-1,3-benzodioxol-4-yl)-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazolin-4-amine (0.140 g, 0.28 mmol ), 5-iodo-1-[(4-methylphenyl)sulfonyl)-1H-pyrazole (0.147 g, 0.42 mmol) and diisopropylamine (0.078 ml, 0.56 mmol) in ethyl acetate (5 ml) was cooled to −20 C under a nitrogen atmosphere... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1cc[nH]n1 | c1cc[nH]n1 | c1cc[nH]n1.c1ccccc1.c1ccc2c(c1)OCO2.c1ccc2ncncc2c1.C1COCC[NH]1 | HI | [Cu]I.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.C(C)(=O)OCC | null | 8 | C#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCOCC4)c(OC)cc23)c2c1OCO2.Cc1ccc(S(=O)(=O)n2nccc2I)cc1>[Cu]I.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.C(C)(=O)OCC>COc1cc2c(Nc3c(Cl)cc(C#Cc4ccnn4S(=O)(=O)c4ccc(C)cc4)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-94371dac08374875a89992117a0ddaef | C#Cc1ccccn1.COc1cc2c(Nc3c(Cl)cc(I)c4c3OCO4)ncnc2cc1OCCCN1CCN(C)C(=O)C1>>COc1cc2c(Nc3c(Cl)cc(C#Cc4ccccn4)c4c3OCO4)ncnc2cc1OCCCN1CCN(C)C(=O)C1 | ClC1=C(C2=C(OCO2)C(=C1)I)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CC(N(CC1)C)=O.C(#C)C1=NC=CC=C1.C(C)(C)NC(C)C>>ClC1=C(C2=C(OCO2)C(=C1)C#CC1=NC=CC=C1)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CC(N(CC1)C)=O | [CH:13]#[C:14][c:15]1[cH:16][cH:17][cH:18][cH:19][n:20]1.I[c:12]1[cH:11][c:9]([Cl:10])[c:8]([NH:7][c:6]2[c:5]3[cH:4][c:3]([O:2][CH3:1])[c:31]([O:32][CH2:33][CH2:34][CH2:35][N:36]4[CH2:37][CH2:38][N:39]([CH3:40])[C:41](=[O:42])[CH2:43]4)[cH:30][c:29]3[n:28][cH:27][n:26]2)[c:22]2[c:21]1[O:25][CH2:24][O:23]2>>[CH3:1][O:2]... | C#Cc1ccccn1.COc1cc2c(Nc3c(Cl)cc(I)c4c3OCO4)ncnc2cc1OCCCN1CCN(C)C(=O)C1 | COc1cc2c(Nc3c(Cl)cc(C#Cc4ccccn4)c4c3OCO4)ncnc2cc1OCCCN1CCN(C)C(=O)C1 | null | [Cu]I.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl | C(C)(=O)OCC | C-C Coupling | Sonogashira alkyne_aryl halide | 4fe05dd9f4e06ca437f6fd540183d70cbf88cbb037b34a93217c201e7139cd32 | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | O=C1CN(CCCOc2ccc3c(Nc4ccc(C#Cc5ccccn5)c5c4OCO5)ncnc3c2)CCN1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1.[#7;a:9]:[c:10]-[C:11]#[CH;D1;+0:12]>>[#7;a:9]:[c:10]-[C:11]#[C;H0;D2;+0:12]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1 | 35 | [{"value": 35.0, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CC1=NC=CC=C1)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CC(N(CC1)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.5, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CC1=NC=CC=C1)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CC(N(CC1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_d... | null | null | 8 | HOUR | A solution of 4-[3-({4-[(5-chloro-7-iodo-1,3-benzodioxol-4-yl)amino]-6-methoxyquinazolin-7-yl}oxy)propyl]-1-methylpiperazin-2-one (0.17 g, 0.27 mmol), 2-ethynyl pyridine (0.056 g, 0.54 mmol) and diisopropylamine (0.075 ml, 0.54 mmol) in ethyl acetate (5 ml) was cooled to −20 C under a nitrogen atmosphere. To this was a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | c1ccncc1.c1ccc2c(c1)OCO2.c1ccc2ncncc2c1.C1C[NH]CC[NH]1 | HI | [Cu]I.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.C(C)(=O)OCC | null | 8 | C#Cc1ccccn1.COc1cc2c(Nc3c(Cl)cc(I)c4c3OCO4)ncnc2cc1OCCCN1CCN(C)C(=O)C1>[Cu]I.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.C(C)(=O)OCC>COc1cc2c(Nc3c(Cl)cc(C#Cc4ccccn4)c4c3OCO4)ncnc2cc1OCCCN1CCN(C)C(=O)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7f3d20b3e59140b39dfe448353bd2730 | CC(C)(O)C#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2ncnc(Cl)c2cc1OC>>COc1cc2ncnc(Nc3c(Cl)cc(C#CC(C)(C)O)c4c3OCO4)c2cc1OC | C[Si](C)(C)[N-][Si](C)(C)C.[Na+].O1CCCC1.NC1=C(C=C(C2=C1OCO2)C#CC(C)(O)C)Cl.ClC1=NC=NC2=CC(=C(C=C12)OC)OC>>ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OC)C#CC(C)(O)C | [NH2:10][c:11]1[c:12]([Cl:13])[cH:14][c:15]([C:16]#[C:17][C:18]([CH3:19])([CH3:20])[OH:21])[c:22]2[c:23]1[O:24][CH2:25][O:26]2.Cl[c:9]1[n:8][cH:7][n:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:29]([O:30][CH3:31])[cH:28][c:27]21>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8][c:9]([NH:10][c:11]3[c:12]([Cl:13])[cH:14][c:15]([C:1... | CC(C)(O)C#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2ncnc(Cl)c2cc1OC | COc1cc2ncnc(Nc3c(Cl)cc(C#CC(C)(C)O)c4c3OCO4)c2cc1OC | null | null | [Cl-].[NH4+].CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ncnc3ccccc23)c2c(c1)OCO2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:9]-[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13] | 50.8 | [{"value": 50.8, "product": "ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OC)C#CC(C)(O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | A solution of sodium bis(trimethylsilyl)amide (1.5 ml) in tetrahydrofuran (1.0M, 1.5 mmol) was added over 5 min. to a stirred mixture of 4-(7-amino-6-chloro-1,3-benzodioxol-4yl)-2-methylbut-3-yn-2-ol (0.186 g) and 4-chloro-6,7-dimethoxyquinazoline (0.150 g) in DMF (6.5 ml) cooled to 0° C. under a nitrogen atmosphere. T... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccc2c(c1)OCO2 | HCl | [Cl-].[NH4+].CN(C)C=O | 0 | 1 | CC(C)(O)C#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2ncnc(Cl)c2cc1OC>[Cl-].[NH4+].CN(C)C=O>COc1cc2ncnc(Nc3c(Cl)cc(C#CC(C)(C)O)c4c3OCO4)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-08d35b9850c3446c9808c062d9860307 | CNC(=O)COCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2ncnc(Cl)c2cc1OC>>CNC(=O)COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OC)c(OC)cc23)c2c1OCO2 | C[Si](C)(C)[N-][Si](C)(C)C.[Na+].O1CCCC1.NC1=C(C=C(C2=C1OCO2)C#CCOCC(=O)NC)Cl.ClC1=NC=NC2=CC(=C(C=C12)OC)OC>>ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OC)C#CCOCC(=O)NC | [CH3:1][NH:2][C:3](=[O:4])[CH2:5][O:6][CH2:7][C:8]#[C:9][c:10]1[cH:11][c:12]([Cl:13])[c:14]([NH2:15])[c:30]2[c:31]1[O:32][CH2:33][O:34]2.Cl[c:16]1[n:17][cH:18][n:19][c:20]2[cH:21][c:22]([O:23][CH3:24])[c:25]([O:26][CH3:27])[cH:28][c:29]12>>[CH3:1][NH:2][C:3](=[O:4])[CH2:5][O:6][CH2:7][C:8]#[C:9][c:10]1[cH:11][c:12]([Cl... | CNC(=O)COCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2ncnc(Cl)c2cc1OC | CNC(=O)COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OC)c(OC)cc23)c2c1OCO2 | null | null | [Cl-].[NH4+].CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ncnc3ccccc23)c2c(c1)OCO2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:9]-[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13] | 39.3 | [{"value": 39.3, "product": "ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OC)C#CCOCC(=O)NC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1.25 | HOUR | A solution of sodium bis(trimethylsilyl)amide (1.23 ml) in tetrahydrofuran (1.0M, 1.23 mmol) was added over 5 min. to a stirred mixture of 2-{[3-(7-amino-6-chloro-1,3-benzodioxol-4-yl)prop-2-yn-1-yl]oxy}-N-methylacetamide (0.182 g) and 4chloro-6,7-dimethoxyquinazoline (0.125 g) in DMF (6.0 ml) cooled to 0° C. under a n... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccc2c(c1)OCO2 | HCl | [Cl-].[NH4+].CN(C)C=O | 0 | 1.25 | CNC(=O)COCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2ncnc(Cl)c2cc1OC>[Cl-].[NH4+].CN(C)C=O>CNC(=O)COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OC)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d807c194d5f2450b9a0e3beb2c146ef9 | CN(C)C(=O)COCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2ncnc(Cl)c2cc1OC>>COc1cc2ncnc(Nc3c(Cl)cc(C#CCOCC(=O)N(C)C)c4c3OCO4)c2cc1OC | C[Si](C)(C)[N-][Si](C)(C)C.[Na+].O1CCCC1.NC1=C(C=C(C2=C1OCO2)C#CCOCC(=O)N(C)C)Cl.ClC1=NC=NC2=CC(=C(C=C12)OC)OC>>ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OC)C#CCOCC(=O)N(C)C | [NH2:10][c:11]1[c:12]([Cl:13])[cH:14][c:15]([C:16]#[C:17][CH2:18][O:19][CH2:20][C:21](=[O:22])[N:23]([CH3:24])[CH3:25])[c:26]2[c:27]1[O:28][CH2:29][O:30]2.Cl[c:9]1[n:8][cH:7][n:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:33]([O:34][CH3:35])[cH:32][c:31]21>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8][c:9]([NH:10][c:11]3[c:12... | CN(C)C(=O)COCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2ncnc(Cl)c2cc1OC | COc1cc2ncnc(Nc3c(Cl)cc(C#CCOCC(=O)N(C)C)c4c3OCO4)c2cc1OC | null | null | [Cl-].[NH4+].CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ncnc3ccccc23)c2c(c1)OCO2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:9]-[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13] | 34.8 | [{"value": 34.8, "product": "ClC=1C=C(C2=C(OCO2)C1NC1=NC=NC2=CC(=C(C=C12)OC)OC)C#CCOCC(=O)N(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | A solution of sodium bis(trimethylsilyl)amide (1.3 ml) in tetrahydrofuran (1.0M, 1.3 mmol) was added over 5 minutes to a stirred mixture of 2-{[3-(7-amino-6-chloro-1,3-benzodioxol-4-yl)prop-2-yn-1-yl]oxy}-N,N-dimethylacetamide (0.200 g) and 4-chloro-6,7-dimethoxyquinazoline (0.132 g) in DMF (5.7 ml) cooled to 0° C. und... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccc2c(c1)OCO2 | HCl | [Cl-].[NH4+].CN(C)C=O | 0 | null | CN(C)C(=O)COCC#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2ncnc(Cl)c2cc1OC>[Cl-].[NH4+].CN(C)C=O>COc1cc2ncnc(Nc3c(Cl)cc(C#CCOCC(=O)N(C)C)c4c3OCO4)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f77a65b8fc344d2fada7b2f3d4e3e5ad | C#CCOCC(=O)Cl.CNC>>C#CCOCC(=O)N(C)C | C(C#C)OCC(=O)Cl.CNC>>CN(C(COCC#C)=O)C | Cl[C:6]([CH2:5][O:4][CH2:3][C:2]#[CH:1])=[O:7].[NH:8]([CH3:9])[CH3:10]>>[CH:1]#[C:2][CH2:3][O:4][CH2:5][C:6](=[O:7])[N:8]([CH3:9])[CH3:10] | C#CCOCC(=O)Cl.CNC | C#CCOCC(=O)N(C)C | null | null | O1CCCC1 | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7]>>[#8:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:6](-[C;D1;H3:5])-[C;D1;H3:7] | null | [] | null | null | null | null | Prop-2-ynyloxyacetyl chloride (1.74 g) in tetrahydrofuran (20 ml) was added dropwise over 5 min. to a stirred solution of dimethylamine (12 ml of 33% solution in ethanol) in tetrahydrofuran (15 ml) at ambient temperature. After 30 minutes the solvent was evaporated and the residue was partitioned between saturated aque... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | null | HCl | O1CCCC1 | null | null | C#CCOCC(=O)Cl.CNC>O1CCCC1>C#CCOCC(=O)N(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9a1a3174c3a84c88a3ce45c1227eb5c7 | C#CCOCC(=O)N(C)C.Nc1c(Cl)cc(I)c2c1OCO2>>CN(C)C(=O)COCC#Cc1cc(Cl)c(N)c2c1OCO2 | C(C)(C)NC(C)C.ClC1=C(C2=C(OCO2)C(=C1)I)N.CN(C(COCC#C)=O)C>>NC1=C(C=C(C2=C1OCO2)C#CCOCC(=O)N(C)C)Cl | [CH3:1][N:2]([CH3:3])[C:4](=[O:5])[CH2:6][O:7][CH2:8][C:9]#[CH:10].I[c:11]1[cH:12][c:13]([Cl:14])[c:15]([NH2:16])[c:17]2[c:18]1[O:19][CH2:20][O:21]2>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[CH2:6][O:7][CH2:8][C:9]#[C:10][c:11]1[cH:12][c:13]([Cl:14])[c:15]([NH2:16])[c:17]2[c:18]1[O:19][CH2:20][O:21]2 | C#CCOCC(=O)N(C)C.Nc1c(Cl)cc(I)c2c1OCO2 | CN(C)C(=O)COCC#Cc1cc(Cl)c(N)c2c1OCO2 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | C(C)(=O)OCC | C-C Coupling | Sonogashira alkyne_aryl halide | 4fe05dd9f4e06ca437f6fd540183d70cbf88cbb037b34a93217c201e7139cd32 | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccc2c(c1)OCO2 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1.[C:9]-[C:10]#[CH;D1;+0:11]>>[C:9]-[C:10]#[C;H0;D2;+0:11]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1 | 81.9 | [{"value": 81.9, "product": "NC1=C(C=C(C2=C1OCO2)C#CCOCC(=O)N(C)C)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -20 | CELSIUS | null | null | Bis(triphenylphosphine)palladium(II) chloride (0.236 g), cuprous iodide (0.96 g) and diisopropylamine (0.47 ml) were added to a stirred solution of 5-chloro-7-iodo-1,3-benzodioxol-4-amine (0.500 g) and N,N-dimethyl-2-(prop-2-yn-1-yloxy)acetamide (0.474 g) in ethyl acetate (8 ml) cooled to −20° C. under a nitrogen atmos... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | HI | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.C(C)(=O)OCC | -20 | null | C#CCOCC(=O)N(C)C.Nc1c(Cl)cc(I)c2c1OCO2>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.C(C)(=O)OCC>CN(C)C(=O)COCC#Cc1cc(Cl)c(N)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ff904252872842a3a22a3f89f7307143 | COC(C)C#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2ncnc(Cl)c2cc1OC>>COc1cc2ncnc(Nc3c(Cl)cc(C#CC(C)OC)c4c3OCO4)c2cc1OC | C[Si](C)(C)[N-][Si](C)(C)C.[Na+].O1CCCC1.ClC1=C(C2=C(OCO2)C(=C1)C#CC(C)OC)N.ClC1=NC=NC2=CC(=C(C=C12)OC)OC>>ClC1=C(C2=C(OCO2)C(=C1)C#CC(C)OC)NC1=NC=NC2=CC(=C(C=C12)OC)OC | [NH2:10][c:11]1[c:12]([Cl:13])[cH:14][c:15]([C:16]#[C:17][CH:18]([CH3:19])[O:20][CH3:21])[c:22]2[c:23]1[O:24][CH2:25][O:26]2.Cl[c:9]1[n:8][cH:7][n:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:29]([O:30][CH3:31])[cH:28][c:27]21>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8][c:9]([NH:10][c:11]3[c:12]([Cl:13])[cH:14][c:15]([C:16]... | COC(C)C#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2ncnc(Cl)c2cc1OC | COc1cc2ncnc(Nc3c(Cl)cc(C#CC(C)OC)c4c3OCO4)c2cc1OC | null | null | [Cl-].[NH4+].CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ncnc3ccccc23)c2c(c1)OCO2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:9]-[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13] | null | [] | 0 | CELSIUS | null | null | A solution of sodium bis(trimethylsilyl)amide (1.7 ml) in tetrahydrofuran (1.0M, 1.7 mmol) was added over 5 minutes to a stirred mixture of 5-chloro-7-(3-methoxybut-1-yn-1-yl)-1,3-benzodioxol-4-amine (0.211 g) and 4-chloro-6,7-dimethoxyquinazoline (0.170 g) in DMF (7.0 ml) cooled to 0° C. under a nitrogen atmosphere; t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccc2c(c1)OCO2 | HCl | [Cl-].[NH4+].CN(C)C=O | 0 | null | COC(C)C#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2ncnc(Cl)c2cc1OC>[Cl-].[NH4+].CN(C)C=O>COc1cc2ncnc(Nc3c(Cl)cc(C#CC(C)OC)c4c3OCO4)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-810320a78d6743a383ca32af82ebd6f9 | COC(C)C#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1>>COc1cc2c(Nc3c(Cl)cc(C#CC(C)OC)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | C[Si](C)(C)[N-][Si](C)(C)C.[Na+].O1CCCC1.ClC1=C(C2=C(OCO2)C(=C1)C#CC(C)OC)N.ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1>>ClC1=C(C2=C(OCO2)C(=C1)C#CC(C)OC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1 | [NH2:7][c:8]1[c:9]([Cl:10])[cH:11][c:12]([C:13]#[C:14][CH:15]([CH3:16])[O:17][CH3:18])[c:19]2[c:20]1[O:21][CH2:22][O:23]2.Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:29]([O:30][CH2:31][CH2:32][CH2:33][N:34]3[CH2:35][CH2:36][O:37][CH2:38][CH2:39]3)[cH:28][c:27]2[n:26][cH:25][n:24]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH... | COC(C)C#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1 | COc1cc2c(Nc3c(Cl)cc(C#CC(C)OC)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | null | null | [Cl-].[NH4+].CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ncnc3cc(OCCCN4CCOCC4)ccc23)c2c(c1)OCO2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:9]-[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13] | null | [] | 0 | CELSIUS | null | null | A solution of sodium bis(trimethylsilyl)amide (1.5 ml) in tetrahydrofuran (1.0M, 1.5 mmol) was added over 5 min. to a stirred mixture of 5-chloro-7-(3-methoxybut-1-yn-1-yl)-1,3-benzodioxol-4-yl-amine (0.190 g) and 4-chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline (0.230 g) in DMF (6.5 ml) cooled to 0° C. under ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2c(c1)OCO2.c1ccc2ncncc2c1.C1COCC[NH]1 | HCl | [Cl-].[NH4+].CN(C)C=O | 0 | null | COC(C)C#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1>[Cl-].[NH4+].CN(C)C=O>COc1cc2c(Nc3c(Cl)cc(C#CC(C)OC)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8859fcd3f88f459ea056c4b215b258a4 | C1CCOC1.CN(C)C=O.COC(C)C#Cc1cc(Br)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCCl.[NH4+]>>COc1cc2c(Nc3c(Br)cc(C#CC(C)OC)c4c3OCO4)ncnc2cc1OCCCN1CCN(C)C(=O)C1 | C[Si](C)(C)[N-][Si](C)(C)C.[Na+].O1CCCC1.BrC1=C(C2=C(OCO2)C(=C1)C#CC(C)OC)N.ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCCl.CN(C=O)C.[Cl-].[NH4+].CCCC(C)C>>BrC1=C(C2=C(OCO2)C(=C1)C#CC(C)OC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CC(N(CC1)C)=O | C1O[CH2:41]C[CH2:35]1.[CH3:36][N:37]([CH3:38])[CH:39]=[O:40].[NH2:7][c:8]1[c:9]([Br:10])[cH:11][c:12]([C:13]#[C:14][CH:15]([CH3:16])[O:17][CH3:18])[c:19]2[c:20]1[O:21][CH2:22][O:23]2.Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:29]([O:30][CH2:31][CH2:32][CH2:33]Cl)[cH:28][c:27]2[n:26][cH:25][n:24]1.[NH4+:34]>>[CH3:1][O:2]... | C1CCOC1.CN(C)C=O.COC(C)C#Cc1cc(Br)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCCl.[NH4+] | COc1cc2c(Nc3c(Br)cc(C#CC(C)OC)c4c3OCO4)ncnc2cc1OCCCN1CCN(C)C(=O)C1 | null | null | C(C)(=O)OCC | C-C Coupling | OtherReaction | 7a905e4ae352ea7745bd5ba555bbc4d3173d90bd8601de496d2bcd5ebcdee28a | 6c9a375afe543068907fb0a7d4a0161a350e86960cb15c05f314d3d6c20ec665 | O=C1CN(CCCOc2ccc3c(Nc4cccc5c4OCO5)ncnc3c2)CCN1 | C1-O-[CH2;D2;+0:1]-C-[CH2;D2;+0:2]-1.Cl-[CH2;D2;+0:3]-[C:4]-[C:5].Cl-[c;H0;D3;+0:6]1:[#7;a:7]:[c:8]:[#7;a:9]:[c:10](:[c:11]):[c:12]:1:[c:13].[#8:14]-[c:15]:[c:16](-[NH2;D1;+0:17]):[c:18].[C;D1;H3:19]-[#7:20](-[CH3;D1;+0:21])-[CH;D2;+0:22]=[O;D1;H0:23].[NH4+;D0:24]>>[#8:14]-[c:15]:[c:16](-[NH;D2;+0:17]-[c;H0;D3;+0:6]1:[... | null | [] | null | null | 8 | HOUR | A solution of sodium bis(trimethylsilyl)amide (1.4 ml) in tetrahydrofuran (1.0M, 1.4 mmol) was added dropwise to an ice-cold solution of 5-bromo-7-(3-methoxybut-1-yn-1-yl)-1,3-benzodioxol-4-amine (0.208 g, 0.70 mmol) and 4-chloro-7-(3-chloropropoxy)-6-methoxyquinazoline (0.201 g, 0.70 mmol) in dimethylformamide (10 ml)... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary halide.Ether.Tertiary amide.Primary amine | Tertiary amide.Secondary amine.Tertiary amine | C1CCOC1.c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1C[NH]CC[NH]1 | c1ccc2c(c1)OCO2.c1ccc2ncncc2c1.C1C[NH]CC[NH]1 | HCl | C(C)(=O)OCC | null | 8 | C1CCOC1.CN(C)C=O.COC(C)C#Cc1cc(Br)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCCl.[NH4+]>C(C)(=O)OCC>COc1cc2c(Nc3c(Br)cc(C#CC(C)OC)c4c3OCO4)ncnc2cc1OCCCN1CCN(C)C(=O)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a0c39120b0024a4aacdfde0cb07287d5 | C1COCCN1.COc1cc2c(Nc3c(Br)cc(C#CC(C)OC)c4c3OCO4)ncnc2cc1OCCCCl>>COc1cc2c(Nc3c(Br)cc(C#CC(C)OC)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | BrC1=C(C2=C(OCO2)C(=C1)C#CC(C)OC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCCl.N1CCOCC1>>BrC1=C(C2=C(OCO2)C(=C1)C#CC(C)OC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1 | [NH:34]1[CH2:35][CH2:36][O:37][CH2:38][CH2:39]1.Cl[CH2:33][CH2:32][CH2:31][O:30][c:29]1[c:3]([O:2][CH3:1])[cH:4][c:5]2[c:6]([NH:7][c:8]3[c:9]([Br:10])[cH:11][c:12]([C:13]#[C:14][CH:15]([CH3:16])[O:17][CH3:18])[c:19]4[c:20]3[O:21][CH2:22][O:23]4)[n:24][cH:25][n:26][c:27]2[cH:28]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH... | C1COCCN1.COc1cc2c(Nc3c(Br)cc(C#CC(C)OC)c4c3OCO4)ncnc2cc1OCCCCl | COc1cc2c(Nc3c(Br)cc(C#CC(C)OC)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 2bad30dcdb0a20edb8ce877f072b133eedfd870621da393ec393128bfee00977 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc(Nc2ncnc3cc(OCCCN4CCOCC4)ccc23)c2c(c1)OCO2 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[#8:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#8:4]-[C:9]-[C:8]-1 | null | [] | null | null | 8 | HOUR | A mixture of N-[5-bromo-7-(3-methoxybut-1-yn-1-yl)-1,3-benzodioxol-4-yl]-7-(3-chloropropoxy)-6-methoxyquinazolin-4-amine (0.12 g, 0.22 mmol) in morpholine (2 ml) was heated at 40 C for 5 hours and then stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue purified directl... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1COCCN1 | C1COCC[NH]1 | c1ccc2c(c1)OCO2.c1ccc2ncncc2c1.C1COCC[NH]1 | HCl | null | null | 8 | C1COCCN1.COc1cc2c(Nc3c(Br)cc(C#CC(C)OC)c4c3OCO4)ncnc2cc1OCCCCl>>COc1cc2c(Nc3c(Br)cc(C#CC(C)OC)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3401318c08d849d3a0dc22f4f2e93226 | C1CCOC1.CN(C)C=O.COCC#Cc1cc(Br)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCCl.[NH4+]>>COCC#Cc1cc(Br)c(Nc2ncnc3cc(OCCCN4CCN(C)C(=O)C4)c(OC)cc23)c2c1OCO2 | C[Si](C)(C)[N-][Si](C)(C)C.[Na+].O1CCCC1.BrC1=C(C2=C(OCO2)C(=C1)C#CCOC)N.ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCCl.CN(C=O)C.[Cl-].[NH4+].CCCC(C)C>>BrC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CC(N(CC1)C)=O | C1O[CH2:30]C[CH2:24]1.[CH3:25][N:26]([CH3:27])[CH:28]=[O:29].[CH3:1][O:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][c:8]([Br:9])[c:10]([NH2:11])[c:36]2[c:37]1[O:38][CH2:39][O:40]2.Cl[c:12]1[n:13][cH:14][n:15][c:16]2[cH:17][c:18]([O:19][CH2:20][CH2:21][CH2:22]Cl)[c:31]([O:32][CH3:33])[cH:34][c:35]12.[NH4+:23]>>[CH3:1][O:2][CH2:3][C... | C1CCOC1.CN(C)C=O.COCC#Cc1cc(Br)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCCl.[NH4+] | COCC#Cc1cc(Br)c(Nc2ncnc3cc(OCCCN4CCN(C)C(=O)C4)c(OC)cc23)c2c1OCO2 | null | null | C(C)(=O)OCC | C-C Coupling | OtherReaction | 7a905e4ae352ea7745bd5ba555bbc4d3173d90bd8601de496d2bcd5ebcdee28a | 6c9a375afe543068907fb0a7d4a0161a350e86960cb15c05f314d3d6c20ec665 | O=C1CN(CCCOc2ccc3c(Nc4cccc5c4OCO5)ncnc3c2)CCN1 | C1-O-[CH2;D2;+0:1]-C-[CH2;D2;+0:2]-1.Cl-[CH2;D2;+0:3]-[C:4]-[C:5].Cl-[c;H0;D3;+0:6]1:[#7;a:7]:[c:8]:[#7;a:9]:[c:10](:[c:11]):[c:12]:1:[c:13].[#8:14]-[c:15]:[c:16](-[NH2;D1;+0:17]):[c:18].[C;D1;H3:19]-[#7:20](-[CH3;D1;+0:21])-[CH;D2;+0:22]=[O;D1;H0:23].[NH4+;D0:24]>>[#8:14]-[c:15]:[c:16](-[NH;D2;+0:17]-[c;H0;D3;+0:6]1:[... | null | [] | null | null | 8 | HOUR | A solution of sodium bis(trimethylsilyl)amide (0.5 ml) in tetrahydrofuran (1.0M, 0.5 mmol) was added dropwise to an ice-cold solution of [5-bromo-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-yl]amine (0.073 g, 0.25 mmol) and 4-chloro-7-(3-chloropropoxy)-6-methoxyquinazoline (0.076 g, 0.26 mmol) in dimethylformamide (5... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary halide.Ether.Tertiary amide.Primary amine | Tertiary amide.Secondary amine.Tertiary amine | C1CCOC1.c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1C[NH]CC[NH]1 | c1ccc2ncncc2c1.C1C[NH]CC[NH]1.c1ccc2c(c1)OCO2 | HCl | C(C)(=O)OCC | null | 8 | C1CCOC1.CN(C)C=O.COCC#Cc1cc(Br)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCCl.[NH4+]>C(C)(=O)OCC>COCC#Cc1cc(Br)c(Nc2ncnc3cc(OCCCN4CCN(C)C(=O)C4)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2467d81877434cfe8187954255027fdb | CC(=O)N1CCNCC1.COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2>>COCC#Cc1cc(Cl)c(Nc2nc(OCCCN3CCN(C(C)=O)CC3)nc3ccc(OC)cc23)c2c1OCO2 | ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCCl.C(C)(=O)N1CCNCC1.[I-].[Na+]>>C(C)(=O)N1CCN(CC1)CCCOC1=NC2=CC=C(C=C2C(=N1)NC1=C(C=C(C=2OCOC21)C#CCOC)Cl)OC | [NH:19]1[CH2:20][CH2:21][N:22]([C:23]([CH3:24])=[O:25])[CH2:26][CH2:27]1.Cl[CH2:18][CH2:17][CH2:16][O:15][c:31]1[cH:30][c:29]2[n:28][cH:14][n:13][c:12]([NH:11][c:10]3[c:8]([Cl:9])[cH:7][c:6]([C:5]#[C:4][CH2:3][O:2][CH3:1])[c:38]4[c:37]3[O:41][CH2:40][O:39]4)[c:36]2[cH:35][c:32]1[O:33][CH3:34]>>[CH3:1][O:2][CH2:3][C:4]#... | CC(=O)N1CCNCC1.COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2 | COCC#Cc1cc(Cl)c(Nc2nc(OCCCN3CCN(C(C)=O)CC3)nc3ccc(OC)cc23)c2c1OCO2 | null | null | ClCCl.COCCO | Heteroatom Alkylation and Arylation | OtherReaction | c620d998a42366876f86e196a0de55450227750f3d51bde1b7d4f1de6fa9bf67 | ee76bd6f46dec2833a5164047e308d22b0c2f15c69808d0f3c01aa1cb3e372db | c1cc(Nc2nc(OCCCN3CCNCC3)nc3ccccc23)c2c(c1)OCO2 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[c:6]:[c:7]2:[#7;a:8]:[cH;D2;+0:9]:[#7;a:10]:[c:11]:[c:12]:2:[c:13]:[c:14]:1-[#8:15].[#7:16]1-[C:17]-[C:18]-[NH;D2;+0:19]-[C:20]-[C:21]-1>>[#8:15]-[c:14]1:[c:13]:[c:12]2:[c:11]:[#7;a:10]:[c;H0;D3;+0:9](-[O;H0;D2;+0:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:19]3... | 145 | [{"value": 145.0, "product": "C(C)(=O)N1CCN(CC1)CCCOC1=NC2=CC=C(C=C2C(=N1)NC1=C(C=C(C=2OCOC21)C#CCOC)Cl)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 105 | CELSIUS | null | null | N-[5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-yl]-7-(3-chloropropoxy)-6-methoxyquinazolin-4-amine (0.158 g) was dissolved in 2-methoxyethanol (5 ml) and then N-acetylpiperazine (0.600 g) was added and the mixture heated to 105° C. A small amount of sodium iodide was added to the reaction mixture, and heatin... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Secondary amine | Ether.Tertiary amine | C1CNCC[NH]1.c1ccc2ncncc2c1 | C1C[NH]CC[NH]1.c1ccc2ncncc2c1 | C1C[NH]CC[NH]1.c1ccc2ncncc2c1.c1ccc2c(c1)OCO2 | HCl | ClCCl.COCCO | 105 | null | CC(=O)N1CCNCC1.COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2>ClCCl.COCCO>COCC#Cc1cc(Cl)c(Nc2nc(OCCCN3CCN(C(C)=O)CC3)nc3ccc(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b8a03a1f9a1a4767907e25eca9a9adfa | COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2.OC[C@H]1CCCN1>>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCC[C@@H]4CO)c(OC)cc23)c2c1OCO2 | ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCCl.N1[C@H](CCC1)CO>>ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1[C@H](CCC1)CO | Cl[CH2:22][CH2:21][CH2:20][O:19][c:18]1[cH:17][c:16]2[n:15][cH:14][n:13][c:12]([NH:11][c:10]3[c:8]([Cl:9])[cH:7][c:6]([C:5]#[C:4][CH2:3][O:2][CH3:1])[c:36]4[c:35]3[O:39][CH2:38][O:37]4)[c:34]2[cH:33][c:30]1[O:31][CH3:32].[NH:23]1[CH2:24][CH2:25][CH2:26][C@@H:27]1[CH2:28][OH:29]>>[CH3:1][O:2][CH2:3][C:4]#[C:5][c:6]1[cH:... | COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2.OC[C@H]1CCCN1 | COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCC[C@@H]4CO)c(OC)cc23)c2c1OCO2 | null | null | ClCCl.COCCO | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 19b442dc26882f89f7423416f5e0a16bdb8e48776df57991434a0634e21f0505 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc(Nc2ncnc3cc(OCCCN4CCCC4)ccc23)c2c(c1)OCO2 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]1-[C:6]-[C:7]-[C:8]-[NH;D2;+0:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[C:6]-[C:5]-1-[C:4] | 182.6 | [{"value": 182.6, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1[C@H](CCC1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | null | null | N-[5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-yl]-7-(3-chloropropoxy)-6-methoxyquinazolin-4-amine (0.165 g) was dissolved in 2-methoxyethanol (5 ml) then (R)-(−)-2-pyrrolidinemethanol (0.516 g) was added and the mixture heated to 110° C. for 50 minutes. The reaction mixture was cooled to room temperature an... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccc2ncncc2c1.C1CC[NH]C1.c1ccc2c(c1)OCO2 | HCl | ClCCl.COCCO | 110 | null | COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2.OC[C@H]1CCCN1>ClCCl.COCCO>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCC[C@@H]4CO)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-37691c967c664d6ba8ae9ee5e32c18ff | C1CNCCN1.COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2>>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCNCC4)c(OC)cc23)c2c1OCO2 | ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCCl.N1CCNCC1>>ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCNCC1 | [NH:23]1[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]1.Cl[CH2:22][CH2:21][CH2:20][O:19][c:18]1[cH:17][c:16]2[n:15][cH:14][n:13][c:12]([NH:11][c:10]3[c:8]([Cl:9])[cH:7][c:6]([C:5]#[C:4][CH2:3][O:2][CH3:1])[c:35]4[c:34]3[O:38][CH2:37][O:36]4)[c:33]2[cH:32][c:29]1[O:30][CH3:31]>>[CH3:1][O:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][c:8]([... | C1CNCCN1.COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2 | COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCNCC4)c(OC)cc23)c2c1OCO2 | null | null | ClCCl.COCCO | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 61ec49e5207aa33ebff7094bb66b1d997d4af14524931a8b3643ef7a94219a9a | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc(Nc2ncnc3cc(OCCCN4CCNCC4)ccc23)c2c(c1)OCO2 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | 69.3 | [{"value": 69.3, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | null | null | N-[5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-yl]-7-(3-chloropropoxy)-6-methoxyquinazolin-4-amine (0.165 g) was dissolved in 2-methoxyethanol (5 ml) and piperazine (0.586 g) was then added and the mixture heated to 110° C. for 45 minutes. The reaction mixture was cooled to room temperature, diluted with dic... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCCN1 | C1C[NH]CCN1 | c1ccc2ncncc2c1.C1C[NH]CCN1.c1ccc2c(c1)OCO2 | HCl | ClCCl.COCCO | 110 | null | C1CNCCN1.COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2>ClCCl.COCCO>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCNCC4)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-062743da78aa415eb92d53bcf02b9377 | COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2.O=C1CNCCN1>>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCNC(=O)C4)c(OC)cc23)c2c1OCO2 | ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCCl.N1C(CNCC1)=O>>ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CC(NCC1)=O | Cl[CH2:22][CH2:21][CH2:20][O:19][c:18]1[cH:17][c:16]2[n:15][cH:14][n:13][c:12]([NH:11][c:10]3[c:8]([Cl:9])[cH:7][c:6]([C:5]#[C:4][CH2:3][O:2][CH3:1])[c:36]4[c:35]3[O:39][CH2:38][O:37]4)[c:34]2[cH:33][c:30]1[O:31][CH3:32].[NH:23]1[CH2:24][CH2:25][NH:26][C:27](=[O:28])[CH2:29]1>>[CH3:1][O:2][CH2:3][C:4]#[C:5][c:6]1[cH:7]... | COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2.O=C1CNCCN1 | COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCNC(=O)C4)c(OC)cc23)c2c1OCO2 | null | null | ClCCl.COCCO | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 61ec49e5207aa33ebff7094bb66b1d997d4af14524931a8b3643ef7a94219a9a | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1CN(CCCOc2ccc3c(Nc4cccc5c4OCO5)ncnc3c2)CCN1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[C:5]1-[#7:6]-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:5](=[O;D1;H0:4])-[C:10]-1 | 71.7 | [{"value": 71.7, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CC(NCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | null | null | N-[5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-yl]-7-(3-chloropropoxy)-6-methoxyquinazolin-4-amine (0.200 g) was dissolved in 2-methoxyethanol (6 ml) and piperazine-2-one (0.821 g) was then added and the mixture heated to 110° C. for 3 hours. The reaction mixture was cooled to room temperature, diluted with ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCCN1 | C1C[NH]CCN1 | c1ccc2ncncc2c1.C1C[NH]CCN1.c1ccc2c(c1)OCO2 | HCl | ClCCl.COCCO | 110 | null | COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2.O=C1CNCCN1>ClCCl.COCCO>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCNC(=O)C4)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-58cc892b556e4fe9a7a58be9f1319caf | COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2.FCCN1CCNCC1>>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(CCF)CC4)c(OC)cc23)c2c1OCO2 | ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCCl.FCCN1CCNCC1.C(C)(C)N(CC)C(C)C>>ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCN(CC1)CCF | Cl[CH2:22][CH2:21][CH2:20][O:19][c:18]1[cH:17][c:16]2[n:15][cH:14][n:13][c:12]([NH:11][c:10]3[c:8]([Cl:9])[cH:7][c:6]([C:5]#[C:4][CH2:3][O:2][CH3:1])[c:38]4[c:37]3[O:41][CH2:40][O:39]4)[c:36]2[cH:35][c:32]1[O:33][CH3:34].[NH:23]1[CH2:24][CH2:25][N:26]([CH2:27][CH2:28][F:29])[CH2:30][CH2:31]1>>[CH3:1][O:2][CH2:3][C:4]#[... | COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2.FCCN1CCNCC1 | COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(CCF)CC4)c(OC)cc23)c2c1OCO2 | null | null | ClCCl.COCCO | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc(Nc2ncnc3cc(OCCCN4CCNCC4)ccc23)c2c(c1)OCO2 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | 46.7 | [{"value": 46.7, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCN(CC1)CCF", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | null | null | N-[5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-yl]-7-(3-chloropropoxy)-6-methoxyquinazolin-4-amine (0.165 g) was dissolved in 2-methoxyethanol (5 ml) and then fluoroethyl piperazine (0.821 g) was added followed by diisopropylethylamine (0.83 ml) and the mixture heated to 110° C. for 15 hours. The reaction mi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccc2ncncc2c1.C1C[NH]CC[NH]1.c1ccc2c(c1)OCO2 | HCl | ClCCl.COCCO | 110 | null | COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)c(OC)cc23)c2c1OCO2.FCCN1CCNCC1>ClCCl.COCCO>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(CCF)CC4)c(OC)cc23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8ffaa77a8e984dbd916df2b62730caa8 | COCC#Cc1cc(Cl)c(N)c2c1OCO2.Clc1ncnc2cc(OCCCN3CCOCC3)cc(OC3CCOCC3)c12>>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCOCC4)cc(OC4CCOCC4)c23)c2c1OCO2 | C[Si](C)(C)[N-][Si](C)(C)C.[Na+].O1CCCC1.ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)N.ClC1=NC=NC2=CC(=CC(=C12)OC1CCOCC1)OCCCN1CCOCC1.C[Si](C)(C)[N-][Si](C)(C)C.[Na+].O1CCCC1>>ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=CC(=C12)OC1CCOCC1)OCCCN1CCOCC1 | [CH3:1][O:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][c:8]([Cl:9])[c:10]([NH2:11])[c:39]2[c:40]1[O:41][CH2:42][O:43]2.Cl[c:12]1[n:13][cH:14][n:15][c:16]2[cH:17][c:18]([O:19][CH2:20][CH2:21][CH2:22][N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)[cH:29][c:30]([O:31][CH:32]3[CH2:33][CH2:34][O:35][CH2:36][CH2:37]3)[c:38]12>>[CH3:1][O... | COCC#Cc1cc(Cl)c(N)c2c1OCO2.Clc1ncnc2cc(OCCCN3CCOCC3)cc(OC3CCOCC3)c12 | COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCOCC4)cc(OC4CCOCC4)c23)c2c1OCO2 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ncnc3cc(OCCCN4CCOCC4)cc(OC4CCOCC4)c23)c2c(c1)OCO2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:9]-[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13] | 36.2 | [{"value": 36.2, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=CC(=C12)OC1CCOCC1)OCCCN1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -10 | CELSIUS | 90 | MINUTE | A solution of sodium bis(trimethylsilyl)amide (1.28 ml) in tetrahydrofuran (1.0M, 1.28 mmol) was added to a suspension of 5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-amine (0.153 g) and 4-chloro-7-(3-morpholin-4-ylpropoxy)-5-(tetrahydro-2H-pyran-4-yloxy)quinazoline (0.260 g) in DMF (4 ml) that had been coole... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1COCC[NH]1.C1CCOCC1.c1ccc2c(c1)OCO2 | HCl | CN(C)C=O | -10 | 1.5 | COCC#Cc1cc(Cl)c(N)c2c1OCO2.Clc1ncnc2cc(OCCCN3CCOCC3)cc(OC3CCOCC3)c12>CN(C)C=O>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCOCC4)cc(OC4CCOCC4)c23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a5cbadec675348bd8b6d4b2d2eed6ed8 | COCCC#Cc1cc(Cl)c(N)c2c1OCO2.Clc1ncnc2cc(OCCCN3CCOCC3)cc(OC3CCOCC3)c12>>COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCOCC4)cc(OC4CCOCC4)c23)c2c1OCO2 | C[Si](C)(C)[N-][Si](C)(C)C.[Na+].O1CCCC1.ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)N.ClC1=NC=NC2=CC(=CC(=C12)OC1CCOCC1)OCCCN1CCOCC1>>ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=CC(=C12)OC1CCOCC1)OCCCN1CCOCC1 | [CH3:1][O:2][CH2:3][CH2:4][C:5]#[C:6][c:7]1[cH:8][c:9]([Cl:10])[c:11]([NH2:12])[c:40]2[c:41]1[O:42][CH2:43][O:44]2.Cl[c:13]1[n:14][cH:15][n:16][c:17]2[cH:18][c:19]([O:20][CH2:21][CH2:22][CH2:23][N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[cH:30][c:31]([O:32][CH:33]3[CH2:34][CH2:35][O:36][CH2:37][CH2:38]3)[c:39]12>>[... | COCCC#Cc1cc(Cl)c(N)c2c1OCO2.Clc1ncnc2cc(OCCCN3CCOCC3)cc(OC3CCOCC3)c12 | COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCOCC4)cc(OC4CCOCC4)c23)c2c1OCO2 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ncnc3cc(OCCCN4CCOCC4)cc(OC4CCOCC4)c23)c2c(c1)OCO2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:9]-[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13] | 63.2 | [{"value": 63.2, "product": "ClC1=C(C2=C(OCO2)C(=C1)C#CCCOC)NC1=NC=NC2=CC(=CC(=C12)OC1CCOCC1)OCCCN1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -10 | CELSIUS | 90 | MINUTE | A solution of sodium bis(trimethylsilyl)amide (1.10 ml) in tetrahydrofuran (1.0M, 1.10 mmol) was added to a suspension of 5-chloro-7-(4-methoxybut-1-yn-1-yl)-1,3-benzodioxol-4-yl-amine (0.139 g) and 4-chloro-7-(3-morpholin-4-ylpropoxy)-5-(tetrahydro-2H-pyran-4-yloxy)quinazoline (0.223 g) in DMF (5 ml) that had been coo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1COCC[NH]1.C1CCOCC1.c1ccc2c(c1)OCO2 | HCl | CN(C)C=O | -10 | 1.5 | COCCC#Cc1cc(Cl)c(N)c2c1OCO2.Clc1ncnc2cc(OCCCN3CCOCC3)cc(OC3CCOCC3)c12>CN(C)C=O>COCCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCOCC4)cc(OC4CCOCC4)c23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6fba5396839f40eb94389fe8e81638ba | CC(=O)N1CCNCC1.COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)cc(OC(C)C)c23)c2c1OCO2>>COCC#Cc1cc(Cl)c(Nc2nc(OCCCN3CCN(C(C)=O)CC3)nc3cccc(OC(C)C)c23)c2c1OCO2 | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)(=O)N1CCNCC1.COCCO.[I-].[Na+].ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=CC(=C12)OC(C)C)OCCCCl>>C(C)(=O)N1CCN(CC1)CCCOC1=NC2=CC=CC(=C2C(=N1)NC1=C(C=C(C=2OCOC21)C#CCOC)Cl)OC(C)C | [NH:19]1[CH2:20][CH2:21][N:22]([C:23]([CH3:24])=[O:25])[CH2:26][CH2:27]1.Cl[CH2:18][CH2:17][CH2:16][O:15][c:31]1[cH:30][c:29]2[n:28][cH:14][n:13][c:12]([NH:11][c:10]3[c:8]([Cl:9])[cH:7][c:6]([C:5]#[C:4][CH2:3][O:2][CH3:1])[c:40]4[c:39]3[O:43][CH2:42][O:41]4)[c:38]2[c:33]([O:34][CH:35]([CH3:36])[CH3:37])[cH:32]1>>[CH3:1... | CC(=O)N1CCNCC1.COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)cc(OC(C)C)c23)c2c1OCO2 | COCC#Cc1cc(Cl)c(Nc2nc(OCCCN3CCN(C(C)=O)CC3)nc3cccc(OC(C)C)c23)c2c1OCO2 | null | null | ClCCl | Heteroatom Alkylation and Arylation | OtherReaction | c620d998a42366876f86e196a0de55450227750f3d51bde1b7d4f1de6fa9bf67 | ee76bd6f46dec2833a5164047e308d22b0c2f15c69808d0f3c01aa1cb3e372db | c1cc(Nc2nc(OCCCN3CCNCC3)nc3ccccc23)c2c(c1)OCO2 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[O;H0;D2;+0:4]-[c;H0;D3;+0:5]1:[c:6]:[c:7]2:[#7;a:8]:[cH;D2;+0:9]:[#7;a:10]:[c:11]:[c:12]:2:[c:13]:[c:14]:1.[#7:15]1-[C:16]-[C:17]-[NH;D2;+0:18]-[C:19]-[C:20]-1>>[#7:15]1-[C:16]-[C:17]-[N;H0;D3;+0:18](-[CH2;D2;+0:1]-[C:2]-[C:3]-[O;H0;D2;+0:4]-[c;H0;D3;+0:9]2:[#7;a:10]:[c:11]:[c:12]3:[c:13]:... | null | [] | 110 | CELSIUS | 4 | HOUR | A mixture of N-[5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-yl]-7-(3-chloropropoxy)-5-isopropoxyquinazolin-4-amine (0.253 g, as a 1:1.3 wt.:wt. mixture with triphenylphosphine) and N-acetyl piperazine (0.538 g) was dissolved in 2-methoxyethanol. Sodium iodide (0.031 g) was added and the reaction mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Secondary amine | Ether.Tertiary amine | C1CNCC[NH]1.c1ccc2ncncc2c1 | C1C[NH]CC[NH]1.c1ccc2ncncc2c1 | C1C[NH]CC[NH]1.c1ccc2ncncc2c1.c1ccc2c(c1)OCO2 | HCl | ClCCl | 110 | 4 | CC(=O)N1CCNCC1.COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)cc(OC(C)C)c23)c2c1OCO2>ClCCl>COCC#Cc1cc(Cl)c(Nc2nc(OCCCN3CCN(C(C)=O)CC3)nc3cccc(OC(C)C)c23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-edbd85ba39e64e66a26324c30e4b33d9 | C#CCOC.CC(C)Oc1cc(OCCCCl)cc2ncnc(Nc3c(Cl)cc(I)c4c3OCO4)c12>>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)cc(OC(C)C)c23)c2c1OCO2 | C(C)(C)NC(C)C.ClC1=C(C2=C(OCO2)C(=C1)I)NC1=NC=NC2=CC(=CC(=C12)OC(C)C)OCCCCl.COCC#C>>ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=CC(=C12)OC(C)C)OCCCCl | [CH3:1][O:2][CH2:3][C:4]#[CH:5].I[c:6]1[cH:7][c:8]([Cl:9])[c:10]([NH:11][c:12]2[n:13][cH:14][n:15][c:16]3[cH:17][c:18]([O:19][CH2:20][CH2:21][CH2:22][Cl:23])[cH:24][c:25]([O:26][CH:27]([CH3:28])[CH3:29])[c:30]23)[c:31]2[c:32]1[O:33][CH2:34][O:35]2>>[CH3:1][O:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][c:8]([Cl:9])[c:10]([NH:11][c... | C#CCOC.CC(C)Oc1cc(OCCCCl)cc2ncnc(Nc3c(Cl)cc(I)c4c3OCO4)c12 | COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)cc(OC(C)C)c23)c2c1OCO2 | null | [Cu]I | C(C)(=O)OCC | C-C Coupling | Sonogashira alkyne_aryl halide | 4fe05dd9f4e06ca437f6fd540183d70cbf88cbb037b34a93217c201e7139cd32 | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1cc(Nc2ncnc3ccccc23)c2c(c1)OCO2 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1.[C:9]-[C:10]#[CH;D1;+0:11]>>[C:9]-[C:10]#[C;H0;D2;+0:11]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1 | null | [] | -10 | CELSIUS | null | null | A mixture N-(5-chloro-7-iodo-1,3-benzodioxol-4yl)-7-(3-chloropropoxy)-5-isopropoxyquinazolin-4-amine (1.313 g, 1:1 wt.:wt. mixture with triphenylphosphine), 3-methoxy-prop-1-yne (0.19 ml), palladium(II) bis-triphenylphosphine dichloride (0.080 g) and copper (I) iodide (0.022 g) was taken up into ethyl acetate (15 ml) a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | c1ccc2ncncc2c1.c1ccc2c(c1)OCO2 | HI | [Cu]I.C(C)(=O)OCC | -10 | null | C#CCOC.CC(C)Oc1cc(OCCCCl)cc2ncnc(Nc3c(Cl)cc(I)c4c3OCO4)c12>[Cu]I.C(C)(=O)OCC>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)cc(OC(C)C)c23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-adf8a5f18ab64cb8bd065a96ba1a48e4 | C#Cc1ccccn1.CC(C)Oc1cc(OCCCN2CCOCC2)cc2ncnc(Nc3c(Cl)cc(I)c4c3OCO4)c12>>CC(C)Oc1cc(OCCCN2CCOCC2)cc2ncnc(Nc3c(Cl)cc(C#Cc4ccccn4)c4c3OCO4)c12 | C(C)(C)NC(C)C.ClC1=C(C2=C(OCO2)C(=C1)I)NC1=NC=NC2=CC(=CC(=C12)OC(C)C)OCCCN1CCOCC1.C(#C)C1=NC=CC=C1>>ClC1=C(C2=C(OCO2)C(=C1)C#CC1=NC=CC=C1)NC1=NC=NC2=CC(=CC(=C12)OC(C)C)OCCCN1CCOCC1 | [CH:30]#[C:31][c:32]1[cH:33][cH:34][cH:35][cH:36][n:37]1.I[c:29]1[cH:28][c:26]([Cl:27])[c:25]([NH:24][c:23]2[n:22][cH:21][n:20][c:19]3[cH:18][c:7]([O:8][CH2:9][CH2:10][CH2:11][N:12]4[CH2:13][CH2:14][O:15][CH2:16][CH2:17]4)[cH:6][c:5]([O:4][CH:2]([CH3:1])[CH3:3])[c:43]32)[c:39]2[c:38]1[O:42][CH2:41][O:40]2>>[CH3:1][CH:2... | C#Cc1ccccn1.CC(C)Oc1cc(OCCCN2CCOCC2)cc2ncnc(Nc3c(Cl)cc(I)c4c3OCO4)c12 | CC(C)Oc1cc(OCCCN2CCOCC2)cc2ncnc(Nc3c(Cl)cc(C#Cc4ccccn4)c4c3OCO4)c12 | null | [Cu]I | C(C)(=O)OCC | C-C Coupling | Sonogashira alkyne_aryl halide | 4fe05dd9f4e06ca437f6fd540183d70cbf88cbb037b34a93217c201e7139cd32 | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | C(#Cc1ccc(Nc2ncnc3cc(OCCCN4CCOCC4)ccc23)c2c1OCO2)c1ccccn1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1.[#7;a:9]:[c:10]-[C:11]#[CH;D1;+0:12]>>[#7;a:9]:[c:10]-[C:11]#[C;H0;D2;+0:12]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]-[#8:6]-[C:7]-[#8:8]-1 | null | [] | -10 | CELSIUS | null | null | N-(5-chloro-7-iodo-1,3-benzodioxol-4-yl)-5-isopropoxy-7-(3-morpholin-4-ylpropoxy)quinazolin-4-amine (0.162 g), 2-ethynyl pyridine (0.03 ml), palladium(II) bis-triphenylphosphine dichloride (0.020 g) and copper (I) iodide (0.006 g) was taken up into ethyl acetate (5 ml) and cooled to −10° C. This was set to stir rapidly... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | C1COCC[NH]1.c1ccc2ncncc2c1.c1ccncc1.c1ccc2c(c1)OCO2 | HI | [Cu]I.C(C)(=O)OCC | -10 | null | C#Cc1ccccn1.CC(C)Oc1cc(OCCCN2CCOCC2)cc2ncnc(Nc3c(Cl)cc(I)c4c3OCO4)c12>[Cu]I.C(C)(=O)OCC>CC(C)Oc1cc(OCCCN2CCOCC2)cc2ncnc(Nc3c(Cl)cc(C#Cc4ccccn4)c4c3OCO4)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fde45198c2f14d59b06281b87547599f | COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)cc(OC(C)C)c23)c2c1OCO2.O=CN1CCNCC1>>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(C=O)CC4)cc(OC(C)C)c23)c2c1OCO2 | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(=O)N1CCNCC1.[I-].[Na+].ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=CC(=C12)OC(C)C)OCCCCl>>ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=CC(=C12)OC(C)C)OCCCN1CCN(CC1)C=O | Cl[CH2:22][CH2:21][CH2:20][O:19][c:18]1[cH:17][c:16]2[n:15][cH:14][n:13][c:12]([NH:11][c:10]3[c:8]([Cl:9])[cH:7][c:6]([C:5]#[C:4][CH2:3][O:2][CH3:1])[c:39]4[c:38]3[O:42][CH2:41][O:40]4)[c:37]2[c:32]([O:33][CH:34]([CH3:35])[CH3:36])[cH:31]1.[NH:23]1[CH2:24][CH2:25][N:26]([CH:27]=[O:28])[CH2:29][CH2:30]1>>[CH3:1][O:2][CH... | COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)cc(OC(C)C)c23)c2c1OCO2.O=CN1CCNCC1 | COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(C=O)CC4)cc(OC(C)C)c23)c2c1OCO2 | null | null | ClCCl.COCCO | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc(Nc2ncnc3cc(OCCCN4CCNCC4)ccc23)c2c(c1)OCO2 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | null | [] | 110 | CELSIUS | 24 | HOUR | A mixture N-[5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-yl]-7-(3-chloropropoxy)-5-isopropoxyquinazolin-4-amine (0.320 g, as a 1:1.3 wt.:wt. mixture with triphenylphosphine) and N-formyl piperazine (0.69 ml) was dissolved in 2-methoxyethanol (7 ml), then sodium iodide (0.040 g) was added and the reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccc2ncncc2c1.C1C[NH]CC[NH]1.c1ccc2c(c1)OCO2 | HCl | ClCCl.COCCO | 110 | 24 | COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)cc(OC(C)C)c23)c2c1OCO2.O=CN1CCNCC1>ClCCl.COCCO>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(C=O)CC4)cc(OC(C)C)c23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8de7396af30549bcb1281b6304d58282 | CN1CCNCC1=O.COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)cc(OC(C)C)c23)c2c1OCO2>>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(C)C(=O)C4)cc(OC(C)C)c23)c2c1OCO2 | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.CN1C(CNCC1)=O.[I-].[Na+].ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=CC(=C12)OC(C)C)OCCCCl>>ClC1=C(C2=C(OCO2)C(=C1)C#CCOC)NC1=NC=NC2=CC(=CC(=C12)OC(C)C)OCCCN1CC(N(CC1)C)=O | [NH:23]1[CH2:24][CH2:25][N:26]([CH3:27])[C:28](=[O:29])[CH2:30]1.Cl[CH2:22][CH2:21][CH2:20][O:19][c:18]1[cH:17][c:16]2[n:15][cH:14][n:13][c:12]([NH:11][c:10]3[c:8]([Cl:9])[cH:7][c:6]([C:5]#[C:4][CH2:3][O:2][CH3:1])[c:39]4[c:38]3[O:42][CH2:41][O:40]4)[c:37]2[c:32]([O:33][CH:34]([CH3:35])[CH3:36])[cH:31]1>>[CH3:1][O:2][C... | CN1CCNCC1=O.COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)cc(OC(C)C)c23)c2c1OCO2 | COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(C)C(=O)C4)cc(OC(C)C)c23)c2c1OCO2 | null | null | ClCCl.COCCO | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1CN(CCCOc2ccc3c(Nc4cccc5c4OCO5)ncnc3c2)CCN1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1=[O;D1;H0:11]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5](-[C;D1;H3:4])-[C:10](=[O;D1;H0:11])-[C:9]-1 | null | [] | 110 | CELSIUS | 24 | HOUR | A mixture N-[5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-yl]-7-(3-chloropropoxy)-5-isopropoxyquinazolin-4-amine (0.320 g, as a 1:1.3 wt.:wt. mixture with triphenylphosphine) and 1-methylpiperazin-2-one (0.280 g) was dissolved in 2-methoxyethanol (7 ml), then sodium iodide (0.040 g) was added and the reaction... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccc2ncncc2c1.C1C[NH]CC[NH]1.c1ccc2c(c1)OCO2 | HCl | ClCCl.COCCO | 110 | 24 | CN1CCNCC1=O.COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCCl)cc(OC(C)C)c23)c2c1OCO2>ClCCl.COCCO>COCC#Cc1cc(Cl)c(Nc2ncnc3cc(OCCCN4CCN(C)C(=O)C4)cc(OC(C)C)c23)c2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f04c0f5afb224b739c6d8c6d0959da6f | COC(C)(C)C#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1>>COc1cc2c(Nc3c(Cl)cc(C#CC(C)(C)OC)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | C[Si](C)(C)[N-][Si](C)(C)C.[Na+].O1CCCC1.ClC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1.ClC1=C(C2=C(OCO2)C(=C1)C#CC(C)(C)OC)N>>ClC1=C(C2=C(OCO2)C(=C1)C#CC(C)(C)OC)NC1=NC=NC2=CC(=C(C=C12)OC)OCCCN1CCOCC1 | [NH2:7][c:8]1[c:9]([Cl:10])[cH:11][c:12]([C:13]#[C:14][C:15]([CH3:16])([CH3:17])[O:18][CH3:19])[c:20]2[c:21]1[O:22][CH2:23][O:24]2.Cl[c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:30]([O:31][CH2:32][CH2:33][CH2:34][N:35]3[CH2:36][CH2:37][O:38][CH2:39][CH2:40]3)[cH:29][c:28]2[n:27][cH:26][n:25]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2... | COC(C)(C)C#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1 | COc1cc2c(Nc3c(Cl)cc(C#CC(C)(C)OC)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ncnc3cc(OCCCN4CCOCC4)ccc23)c2c(c1)OCO2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:9]-[c:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:13] | null | [] | -15 | CELSIUS | 3 | HOUR | A solution of sodium bis(trimethylsilyl)amide (1.12 ml) in tetrahydrofuran (1.0M, 1.12 mmol) was added to a solution 4-chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline (0.189 g) and 5-chloro-7-(3-methoxy-3-methylbut-1-yn-1-yl)-1,3-benzodioxol-4-amine (0.150 g) in DMF (6 ml) that had been cooled to −15° C. and th... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2c(c1)OCO2.c1ccc2ncncc2c1.C1COCC[NH]1 | HCl | CN(C)C=O | -15 | 3 | COC(C)(C)C#Cc1cc(Cl)c(N)c2c1OCO2.COc1cc2c(Cl)ncnc2cc1OCCCN1CCOCC1>CN(C)C=O>COc1cc2c(Nc3c(Cl)cc(C#CC(C)(C)OC)c4c3OCO4)ncnc2cc1OCCCN1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-84aeba1f2a144fbaa12a6a3c0a7e4780 | CCOC(=O)C(C)(C)Br.O=Cc1cc(OCc2ccccc2)ccc1O>>CCOC(=O)C(C)(C)Oc1ccc(OCc2ccccc2)cc1C=O | C(C1=CC=CC=C1)OC=1C=CC(=C(C=O)C1)O.BrC(C(=O)OCC)(C)C.C([O-])([O-])=O.[Cs+].[Cs+]>>C(C)OC(C(C)(C)OC1=C(C=C(C=C1)OCC1=CC=CC=C1)C=O)=O | Br[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([CH3:7])[CH3:8].[OH:9][c:10]1[cH:11][cH:12][c:13]([O:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[cH:22][c:23]1[CH:24]=[O:25]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])([CH3:8])[O:9][c:10]1[cH:11][cH:12][c:13]([O:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH... | CCOC(=O)C(C)(C)Br.O=Cc1cc(OCc2ccccc2)ccc1O | CCOC(=O)C(C)(C)Oc1ccc(OCc2ccccc2)cc1C=O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 657b1e065fabda84e4d6cc80f4d94ce754af0792c9117981e41887a4384f6981 | 2495a256265ef36132d409a6a3e2bd04c3acda5f236d910f184b0a36a846defe | c1ccc(COc2ccccc2)cc1 | Br-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7].[O;D1;H0:8]=[C:9]-[c:10]:[c:11](-[OH;D1;+0:12]):[c:13]>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[O;H0;D2;+0:12]-[c:11](:[c:13]):[c:10]-[C:9]=[O;D1;H0:8] | 89 | [{"value": 89.0, "product": "C(C)OC(C(C)(C)OC1=C(C=C(C=C1)OCC1=CC=CC=C1)C=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.8, "product": "C(C)OC(C(C)(C)OC1=C(C=C(C=C1)OCC1=CC=CC=C1)C=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-Benzyloxy-2-hydroxy-benzaldehyde (Kappe, T.; Witoszynskyj, T. Arch. Pharm., 1975, 308 (5), 339-346) (2.28 g, 10.0 mmol), ethyl bromoisobutyrate (2.2 mL, 15 mmol), and cesium carbonate (3.26 g, 10.0 mmol) in dry DMF (25 mL) are heated at 80° C. for 18 h. The reaction mixture is cooled and partitioned between water (30... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1.c1ccccc1 | HBr | CN(C)C=O | null | null | CCOC(=O)C(C)(C)Br.O=Cc1cc(OCc2ccccc2)ccc1O>CN(C)C=O>CCOC(=O)C(C)(C)Oc1ccc(OCc2ccccc2)cc1C=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3004087dba1245818291045ae96c8e20 | CCOC(=O)C(C)(C)Oc1ccc(OCc2ccccc2)cc1C=O>>CCOC(=O)C(C)(C)Oc1ccc(O)cc1C | C(C)OC(C(C)(C)OC1=C(C=C(C=C1)OCC1=CC=CC=C1)C=O)=O.[H][H]>>C(C)OC(C(C)(C)OC1=C(C=C(C=C1)O)C)=O | O=[CH:17][c:16]1[c:10]([O:9][C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([CH3:7])[CH3:8])[cH:11][cH:12][c:13]([O:14]Cc2ccccc2)[cH:15]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])([CH3:8])[O:9][c:10]1[cH:11][cH:12][c:13]([OH:14])[cH:15][c:16]1[CH3:17] | CCOC(=O)C(C)(C)Oc1ccc(OCc2ccccc2)cc1C=O | CCOC(=O)C(C)(C)Oc1ccc(O)cc1C | null | [Pd].[Pd] | C(C)O | Reduction | OtherReaction | 43c9b8d8c551aed397ab7c6d0128d779b9b0c4cf5ca57f2825323a1918158246 | b10564889f1c3eb85337edcc1037463f8e2a566aedcc0f9c1d37c51ef608d5c5 | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5](-[O;H0;D2;+0:6]-C-c1:c:c:c:c:c:1):[c:7]>>[CH3;D1;+0:1]-[c:2](:[c:3]):[c:4]:[c:5](-[OH;D1;+0:6]):[c:7] | null | [] | null | null | 6 | HOUR | 2-(4-Benzyloxy-2-formyl-phenoxy)-2-methyl-propionic acid ethyl ester (9.00 g, 26.3 mmol) in ethanol (250 mL) is treated with 5% Pd/C (1.25 g) and hydrogen (60 psi, rt, overnight). Additional 5% Pd/C (1.25 g) is added, and the reaction is continued for 6 h at 40° C. The mixture is filtered and concentrated to a tan oil ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ether | Aromatic alcohol | c1ccccc1 | null | c1ccccc1 | HO- | [Pd].[Pd].C(C)O | null | 6 | CCOC(=O)C(C)(C)Oc1ccc(OCc2ccccc2)cc1C=O>[Pd].[Pd].C(C)O>CCOC(=O)C(C)(C)Oc1ccc(O)cc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-454abcd75c5041b7b5b772144ffb1a23 | C=CCc1cc(OCc2ccccc2)ccc1O>>CCCc1cc(OCc2ccccc2)ccc1O | C(C=C)C1=C(C=CC(=C1)OCC1=CC=CC=C1)O.[H][H]>>C(C1=CC=CC=C1)OC1=CC(=C(C=C1)O)CCC | [CH2:1]=[CH:2][CH2:3][c:4]1[cH:5][c:6]([O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][cH:16][c:17]1[OH:18]>>[CH3:1][CH2:2][CH2:3][c:4]1[cH:5][c:6]([O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][cH:16][c:17]1[OH:18] | C=CCc1cc(OCc2ccccc2)ccc1O | CCCc1cc(OCc2ccccc2)ccc1O | null | [Pd] | C(C)(=O)OCC | Reduction | Hydrogenation (double to single) | bc16a674f12262641e5cd54edc2026446c884c0ddcda2374dddc2ac4d3dae2ab | 6afc5b4ad7d0f8b85f89bd805881fd9206fc3da38639abfb1c97bb82ede31c54 | c1ccc(COc2ccccc2)cc1 | [CH2;D1;+0:1]=[CH;D2;+0:2]-[C:3]-[c:4]>>[CH3;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[c:4] | 56 | [{"value": 56.0, "product": "C(C1=CC=CC=C1)OC1=CC(=C(C=C1)O)CCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Allyl-4-benzyloxyphenol (WO 9728137 A1 19970807, Adams, A. D. et al.) (5.00 g, 20.8 mmol) in ethyl acetate (40 mL) is treated with 5% Pd/C (0.25 g) and hydrogen (1 atm) at ambient temperature for 18 h. The mixture is filtered and concentrated. The crude product is purified on a Biotage medium pressure chromatography ... | 10.6084/m9.figshare.5104873.v1 | null | Allyl | null | null | null | c1ccccc1.c1ccccc1 | null | [Pd].C(C)(=O)OCC | null | null | C=CCc1cc(OCc2ccccc2)ccc1O>[Pd].C(C)(=O)OCC>CCCc1cc(OCc2ccccc2)ccc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-efdc8495de91449ba652f13cfaafb3f8 | CCCc1cc(OCc2ccccc2)ccc1O.CCOC(=O)CBr>>CCCc1cc(OCc2ccccc2)ccc1OCC(=O)OCC | C(C1=CC=CC=C1)OC1=CC(=C(C=C1)O)CCC.[H-].[Na+].BrCC(=O)OCC>>C(C)OC(COC1=C(C=C(C=C1)OCC1=CC=CC=C1)CCC)=O | [CH3:1][CH2:2][CH2:3][c:4]1[cH:5][c:6]([O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][cH:16][c:17]1[OH:18].Br[CH2:19][C:20](=[O:21])[O:22][CH2:23][CH3:24]>>[CH3:1][CH2:2][CH2:3][c:4]1[cH:5][c:6]([O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][cH:16][c:17]1[O:18][CH2:19][C:20](=[O:21])[O:2... | CCCc1cc(OCc2ccccc2)ccc1O.CCOC(=O)CBr | CCCc1cc(OCc2ccccc2)ccc1OCC(=O)OCC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccc(COc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | 97.3 | [{"value": 97.0, "product": "C(C)OC(COC1=C(C=C(C=C1)OCC1=CC=CC=C1)CCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.3, "product": "C(C)OC(COC1=C(C=C(C=C1)OCC1=CC=CC=C1)CCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A solution of 4-benzyloxy-2-propylphenol (0.50 g, 1.94 mmol) in dry DMF (7 mL) is cooled in an ice bath and treated with NaH (0.15 g, 3.8 mmol, 60% oil dispersion). The ice bath is removed, ethyl bromoacetate (0.43 mL, 3.9 mmol) is added, and the mixture is placed in an oil bath (T=85° C.). After 18 h, the reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1.c1ccccc1 | HBr | CN(C)C=O | null | 18 | CCCc1cc(OCc2ccccc2)ccc1O.CCOC(=O)CBr>CN(C)C=O>CCCc1cc(OCc2ccccc2)ccc1OCC(=O)OCC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a41591f745fe4dbda4e541162d2d58ce | CCCc1cc(OCc2ccccc2)ccc1OCC(=O)OCC>>CCCc1cc(O)ccc1OCC(=O)OCC | C(C)OC(COC1=C(C=C(C=C1)OCC1=CC=CC=C1)CCC)=O.[H][H]>>C(C)OC(COC1=C(C=C(C=C1)O)CCC)=O | c1ccc(C[O:7][c:6]2[cH:5][c:4]([CH2:3][CH2:2][CH3:1])[c:10]([O:11][CH2:12][C:13](=[O:14])[O:15][CH2:16][CH3:17])[cH:9][cH:8]2)cc1>>[CH3:1][CH2:2][CH2:3][c:4]1[cH:5][c:6]([OH:7])[cH:8][cH:9][c:10]1[O:11][CH2:12][C:13](=[O:14])[O:15][CH2:16][CH3:17] | CCCc1cc(OCc2ccccc2)ccc1OCC(=O)OCC | CCCc1cc(O)ccc1OCC(=O)OCC | null | [Pd] | C1CCOC1 | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccccc1 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | 57.3 | [{"value": 57.0, "product": "C(C)OC(COC1=C(C=C(C=C1)O)CCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.3, "product": "C(C)OC(COC1=C(C=C(C=C1)O)CCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of (4-benzyloxy-2-propylphenoxy)acetic acid ethyl ester (0.60 g, 1.83 mmol) in THF (15 mL) is treated with 5% Pd/C (75 mg) and hydrogen (60 psi) at ambient temperature for 24 h. The mixture is filtered and concentrated. The crude product is purified by radial chromatography using 15% ethyl acetate in hexanes... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccccc1 | Other | [Pd].C1CCOC1 | null | null | CCCc1cc(OCc2ccccc2)ccc1OCC(=O)OCC>[Pd].C1CCOC1>CCCc1cc(O)ccc1OCC(=O)OCC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2996f51cb4824f62892a991a94ea41bc | BrBr.CCOC(=O)COc1ccc(O)cc1>>CCOC(=O)COc1ccc(O)c(Br)c1 | C(C)OC(COC1=CC=C(C=C1)O)=O.BrBr>>C(C)OC(COC1=CC(=C(C=C1)O)Br)=O | Br[Br:14].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([OH:12])[cH:13][cH:15]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([OH:12])[c:13]([Br:14])[cH:15]1 | BrBr.CCOC(=O)COc1ccc(O)cc1 | CCOC(=O)COc1ccc(O)c(Br)c1 | null | null | C(C)(=O)O | Functional Group Interconversion | Bromination | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccccc1 | Br-[Br;H0;D1;+0:1].[O;D1;H1:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6]:[c:7]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:3](-[O;D1;H1:2]):[c:4] | null | [] | null | null | 5 | MINUTE | To a solution of (4-hydroxy-phenoxy)-acetic acid ethyl ester (0.59 g, 3 mmol) in acetic acid (1.5 mL) is added bromine (0.48 g, 9 mmol) in acetic acid (0.5 mL) at room temperature. After 5 min, solvent is evaporated and purified by column chromatography on silica gel giving the title compound (0.6 g).
Conditions: See r... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | C(C)(=O)O | null | 0.083333 | BrBr.CCOC(=O)COc1ccc(O)cc1>C(C)(=O)O>CCOC(=O)COc1ccc(O)c(Br)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-52a862443021473ca4a7b5731bb612d3 | CCOC(=O)COc1ccccc1.O=S(=O)(O)Cl>>CCOC(=O)COc1ccc(S(=O)(=O)Cl)cc1 | C(C)OC(COC1=CC=CC=C1)=O.ClS(=O)(=O)O>>C(C)OC(COC1=CC=C(C=C1)S(=O)(=O)Cl)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][cH:11][cH:16][cH:17]1.O[S:12](=[O:13])(=[O:14])[Cl:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([S:12](=[O:13])(=[O:14])[Cl:15])[cH:16][cH:17]1 | CCOC(=O)COc1ccccc1.O=S(=O)(O)Cl | CCOC(=O)COc1ccc(S(=O)(=O)Cl)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Aromatic sulfonyl chlorination | 04bb0e110ac9bc3104a40572864ecdd042b39019cff0ea96d1a0ad7c9eb6ecf3 | d32b60b8f9bfd187c6c9f1eef6a22a00f53525a7532b83aba763d5389c9e4280 | c1ccccc1 | O-[S;H0;D4;+0:1](-[Cl;D1;H0:2])(=[O;D1;H0:3])=[O;D1;H0:4].[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[Cl;D1;H0:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:6]:[c:5] | null | [] | 0 | CELSIUS | 30 | MINUTE | Phenoxy-acetic acid ethyl ester (9.1 mL) is added to chlorosulfonic acid (15 mL) at 0° C. dropwise. The reaction is stirred at 0° C. for 30 min, it is allowed to warm to room temperature. After 2 hrs, the reaction mixture is poured into ice, solid product is collected by filtration and dried under vacuum.
Conditions: S... | 10.6084/m9.figshare.5104873.v1 | null | null | Sulfonyl halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | null | 0 | 0.5 | CCOC(=O)COc1ccccc1.O=S(=O)(O)Cl>>CCOC(=O)COc1ccc(S(=O)(=O)Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1bac5980400f422194f5b381ef487e29 | CCOC(=O)COc1ccc(S(=O)(=O)Cl)cc1>>CCOC(=O)COc1ccc(S)cc1 | C(Cl)Cl.C(C)OC(COC1=CC=C(C=C1)S(=O)(=O)Cl)=O.[Sn].Cl>>C(C)OC(COC1=CC=C(C=C1)S)=O | O=[S:12](=O)(Cl)[c:11]1[cH:10][cH:9][c:8]([O:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:14][cH:13]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([SH:12])[cH:13][cH:14]1 | CCOC(=O)COc1ccc(S(=O)(=O)Cl)cc1 | CCOC(=O)COc1ccc(S)cc1 | null | null | O1CCOCC1.C(C)O | Reduction | OtherReaction | 67c58f2128339179ba957163c48f4a4ad5eac877ca5a6bdb7ff20914d4efc174 | fdaccf528edde07917e32c5a4cba468523458b8901959f3cb21411d1f4e7837a | c1ccccc1 | Cl-[S;H0;D4;+0:1](=O)(=O)-[c:2](:[c:3]):[c:4]>>[SH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | To a mixture of (4-chlorosulfonyl-phenoxy)-acetic acid ethyl ester (0.98 g, 3.5 mmol) and tin powder (2.1 g) in ethanol (4.4 mL) is added HCl in dioxane (1.0 M, 4.4 mL) under nitrogen. The mixture is heated to reflux for 2 hrs, it is poured into ice and methylene chloride and filtered. The layers are separated and extr... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Aromatic thiol | null | null | c1ccccc1 | Other | O1CCOCC1.C(C)O | null | null | CCOC(=O)COc1ccc(S(=O)(=O)Cl)cc1>O1CCOCC1.C(C)O>CCOC(=O)COc1ccc(S)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-25921e698a2b4805b0570971a8e2cd08 | COC(=O)CCc1ccc(OCc2ccccc2)cc1C>>COC(=O)CCc1ccc(O)cc1C | COC(CCC1=C(C=C(C=C1)OCC1=CC=CC=C1)C)=O.[H][H]>>COC(CCC1=C(C=C(C=C1)O)C)=O | c1ccc(C[O:11][c:10]2[cH:9][cH:8][c:7]([CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[c:13]([CH3:14])[cH:12]2)cc1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([OH:11])[cH:12][c:13]1[CH3:14] | COC(=O)CCc1ccc(OCc2ccccc2)cc1C | COC(=O)CCc1ccc(O)cc1C | null | [Pd] | CO | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccccc1 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | 93.5 | [{"value": 93.5, "product": "COC(CCC1=C(C=C(C=C1)O)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.4, "product": "COC(CCC1=C(C=C(C=C1)O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-(4-Benzyloxy-2-methyl-phenyl)-propionic acid methyl ester (13.7 g, 48.5 mmol) and Pd/C (5%, 13.7 g) in MeOH (423 mL) is stirred under 60 psi of hydrogen for 24 hrs. Catalyst is filtered off, filtrate is concentrated giving the title compound (8.8 g, 93.5%).
Conditions: See reaction.notes.procedure_detail... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccccc1 | Other | [Pd].CO | null | null | COC(=O)CCc1ccc(OCc2ccccc2)cc1C>[Pd].CO>COC(=O)CCc1ccc(O)cc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f1a45547b0f44f63abaff48e45bcb3bf | COC(=O)CCc1ccc(SC(=O)N(C)C)cc1C>>COC(=O)CCc1ccc(S)cc1C | COC(CCC1=C(C=C(C=C1)SC(N(C)C)=O)C)=O.C[O-].[Na+].Cl>>COC(CCC1=C(C=C(C=C1)S)C)=O | CN(C)C(=O)[S:11][c:10]1[cH:9][cH:8][c:7]([CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[c:13]([CH3:14])[cH:12]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([SH:11])[cH:12][c:13]1[CH3:14] | COC(=O)CCc1ccc(SC(=O)N(C)C)cc1C | COC(=O)CCc1ccc(S)cc1C | null | null | CO.C(C)(=O)OCC | Reduction | OtherReaction | b8de7c0dd998c42f71fbae789bd47547a8833f1078d4106e4c6eaba466ea8b96 | 616235514d65b822291e24d80df126c1e4bd115c2e4fc6cf16de0cb196278e81 | c1ccccc1 | C-N(-C)-C(=O)-[S;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[SH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 118.3 | [{"value": 118.3, "product": "COC(CCC1=C(C=C(C=C1)S)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(4-Dimethylcarbamoylsulfanyl-2-methyl-phenyl)-propionic acid methyl ester (5.01 g, 17.8 mmol) is diluted with methanol (30 mL) and to this is added sodium methoxide (1.7 mL of 4M in methanol, 7.23 mmol). The reaction is heated to reflux under nitrogen and monitored by TLC. After complete conversion, 20 h., the reacti... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Monosulfide | Aromatic thiol | null | null | c1ccccc1 | HO- | CO.C(C)(=O)OCC | null | null | COC(=O)CCc1ccc(SC(=O)N(C)C)cc1C>CO.C(C)(=O)OCC>COC(=O)CCc1ccc(S)cc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-71bfebfd62d04eefb0ddda0d1252ed1c | C=CC(=O)OC.Cc1cc(C(=O)OCc2ccccc2)ccc1Br>>COC(=O)C=Cc1ccc(C(=O)OCc2ccccc2)cc1C | C(C1=CC=CC=C1)OC(C1=CC(=C(C=C1)Br)C)=O.C(C=C)(=O)OC.C(C)(C)N(CC)C(C)C>>C(C1=CC=CC=C1)OC(C1=CC(=C(C=C1)C=CC(=O)OC)C)=O | [CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH2:6].Br[c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21][c:22]1[CH3:23]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21][c:22]1[CH3:2... | C=CC(=O)OC.Cc1cc(C(=O)OCc2ccccc2)ccc1Br | COC(=O)C=Cc1ccc(C(=O)OCc2ccccc2)cc1C | null | null | null | C-C Coupling | Heck terminal vinyl | 55becfded1a3842d5a03bbf3e1610411c659aff0806930400c4db2ef61f9c87f | 4b186811a4930853b446d93d9faa39b267bddb9ce0b8021bda5c5a3b2bc69f0b | O=C(OCc1ccccc1)c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6].[C;D1;H3:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[C:11]=[CH2;D1;+0:12]>>[C;D1;H3:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[C:11]=[CH;D2;+0:12]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6] | 84.7 | [{"value": 84.7, "product": "C(C1=CC=CC=C1)OC(C1=CC(=C(C=C1)C=CC(=O)OC)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | null | null | To a solution of 4-bromo-3-methyl-benzoic acid benzyl ester (36 g, 118 mmol) in propronitrile (1000 mL) is added methyl acrylate (43.3 mL) and diisopropylethyl amine (42 mL), the solution is degassed and filled with nitrogen for three times. To this mixture are added tri-o-tolyl-phosphane (14.5 g) and palladium acetate... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl | null | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HBr | null | 110 | null | C=CC(=O)OC.Cc1cc(C(=O)OCc2ccccc2)ccc1Br>>COC(=O)C=Cc1ccc(C(=O)OCc2ccccc2)cc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b4a5ca69db3d427984917ede25e4f507 | COC(=O)C=Cc1ccc(C(=O)OCc2ccccc2)cc1C>>COC(=O)CCc1ccc(C(=O)O)cc1C | C(C1=CC=CC=C1)OC(C1=CC(=C(C=C1)C=CC(=O)OC)C)=O.[H][H]>>COC(=O)CCC1=C(C=C(C(=O)O)C=C1)C | c1ccc(C[O:13][C:11]([c:10]2[cH:9][cH:8][c:7]([CH:6]=[CH:5][C:3]([O:2][CH3:1])=[O:4])[c:15]([CH3:16])[cH:14]2)=[O:12])cc1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[OH:13])[cH:14][c:15]1[CH3:16] | COC(=O)C=Cc1ccc(C(=O)OCc2ccccc2)cc1C | COC(=O)CCc1ccc(C(=O)O)cc1C | null | [Pd] | CO.C1CCOC1 | Deprotection | OtherReaction | 78930d7433e6433d640c5b6f0cce953654a3456d996aca26fceacd90c40f5cd9 | 4bf3ac17eb3813e3e62e99e65fe1a0df4f10f36bb12b96a2bd9a30e5754b7bfb | c1ccccc1 | [C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D2;+0:5]=[CH;D2;+0:6]-[c:7](:[c:8]):[c:9].[O;D1;H0:10]=[C:11](-[c:12])-[O;H0;D2;+0:13]-C-c1:c:c:c:c:c:1>>[C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9].[O;D1;H0:10]=[C:11](-[OH;D1;+0:13])-[c:12] | 100 | [{"value": 100.0, "product": "COC(=O)CCC1=C(C=C(C(=O)O)C=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.9, "product": "COC(=O)CCC1=C(C=C(C(=O)O)C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4-(2-methoxycarbonyl-vinyl)-3-methyl-benzoic acid benzyl ester (11.6 g, 37.4 mmol) and Pd/C (5%, 1.5 g) in THF (300 mL) and methanol (100 mL) is stirred under 60 psi of hydrogen overnight. Catalyst is filtered off, filtrate is concentrated giving the title compound (8.3 g, 100%).
Conditions: See reaction.n... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Ester | c1ccccc1 | null | c1ccccc1 | Other | [Pd].CO.C1CCOC1 | null | null | COC(=O)C=Cc1ccc(C(=O)OCc2ccccc2)cc1C>[Pd].CO.C1CCOC1>COC(=O)CCc1ccc(C(=O)O)cc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8204aa2b30b14d30acf406aed9bc8d18 | COC(=O)Cc1ccc(OC)cc1C>>COC(=O)Cc1ccc(O)cc1C | O.[Cl-].[Al+3].[Cl-].[Cl-].COC(CC1=C(C=C(C=C1)OC)C)=O.C(C)S>>COC(CC1=C(C=C(C=C1)O)C)=O | C[O:10][c:9]1[cH:8][cH:7][c:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[c:12]([CH3:13])[cH:11]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([OH:10])[cH:11][c:12]1[CH3:13] | COC(=O)Cc1ccc(OC)cc1C | COC(=O)Cc1ccc(O)cc1C | null | null | ClCCl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 2 | HOUR | (4-Methoxy-2-methyl-phenyl)-acetic acid methyl ester (1.5 g, 7.72 mmol) is stirred in dichloromethane (50 mL) at 0 deg. C. Aluminum chloride (4.13 g, 31 mmol) is added followed by ethane thiol (2.9 mL, 38.6 mmol). The resulting mixture is stirred at room temperature for 2 hr. Water (50 mL) is added and the product is e... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1 | Other | ClCCl | null | 2 | COC(=O)Cc1ccc(OC)cc1C>ClCCl>COC(=O)Cc1ccc(O)cc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ad5a36ede7434692a503e4088e4a37a8 | CO.O=C(O)Cc1cccc(O)c1>>COC(=O)Cc1cccc(O)c1 | OC=1C=C(C=CC1)CC(=O)O.CO>>COC(CC1=CC(=CC=C1)O)=O | [CH3:1][OH:2].O[C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]([OH:11])[cH:12]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]([OH:11])[cH:12]1 | CO.O=C(O)Cc1cccc(O)c1 | COC(=O)Cc1cccc(O)c1 | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[C;D1;H3:5]-[OH;D1;+0:6]>>[C;D1;H3:5]-[O;H0;D2;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4] | null | [] | null | null | null | null | (3-Hydroxy-phenyl)-acetic acid (5.0 g, 32.86 mmol) is stirred in methanol (100 mL) and concentrated (98%) sulfuric acid (3.0 mL,) is added. The mixture is heated to reflux 18 hr. The reaction is cooled and concentrated. The residue is diluted with water (100 mL) and extracted with ethyl acetate (3×50 mL). The combined ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CO.O=C(O)Cc1cccc(O)c1>>COC(=O)Cc1cccc(O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-45424f0fe44d455f9b0c0c67eea6351f | CN(C)C(=S)Cl.COC(=O)Cc1cccc(O)c1>>COC(=O)Cc1cccc(OC(=S)N(C)C)c1 | COC(CC1=CC(=CC=C1)O)=O.CN(C(=S)Cl)C.C(C)N(CC)CC>>COC(CC1=CC(=CC=C1)OC(N(C)C)=S)=O | Cl[C:12](=[S:13])[N:14]([CH3:15])[CH3:16].[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]([OH:11])[cH:17]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]([O:11][C:12](=[S:13])[N:14]([CH3:15])[CH3:16])[cH:17]1 | CN(C)C(=S)Cl.COC(=O)Cc1cccc(O)c1 | COC(=O)Cc1cccc(OC(=S)N(C)C)c1 | null | null | O1CCOCC1 | Acylation | Schotten-Baumann to ester | 085dbfd01da3f23432eb68a0c9926226856f71cf39acf52aeac55f77c5219807 | 42727264d4762866b627891a642b01ccb211aee4f45c12cd2bb71e89549be2cf | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[S;D1;H0:2])-[#7:3](-[C;D1;H3:4])-[C;D1;H3:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:4]-[#7:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[S;D1;H0:2])-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | null | null | null | null | A mixture of (3-Hydroxy-phenyl)-acetic acid methyl ester (5.5 g, 33.1 mmol), N,N-dimethyl thiocarbamoyl chloride (5.11 g, 41.38 mmol), triethylamine (9.2 mL, 66.2 mmol), N,N-dimethylamino pyridine (0.4 g, 3.31 mmol) and dioxane (50 mL) is stirred at reflux 18 hr. The mixture is concentrated, partioned between 1M aqueou... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Thioamide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HCl | O1CCOCC1 | null | null | CN(C)C(=S)Cl.COC(=O)Cc1cccc(O)c1>O1CCOCC1>COC(=O)Cc1cccc(OC(=S)N(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eaefda6315aa49f8be75e652650e3d79 | COC(=O)Cc1cccc(SC(=O)N(C)C)c1>>COC(=O)Cc1cccc(S)c1 | COC(CC1=CC(=CC=C1)SC(N(C)C)=O)=O.[OH-].[K+].CO>>COC(CC1=CC(=CC=C1)S)=O | CN(C)C(=O)[S:11][c:10]1[cH:9][cH:8][cH:7][c:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[cH:12]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]([SH:11])[cH:12]1 | COC(=O)Cc1cccc(SC(=O)N(C)C)c1 | COC(=O)Cc1cccc(S)c1 | null | null | O | Reduction | OtherReaction | b8de7c0dd998c42f71fbae789bd47547a8833f1078d4106e4c6eaba466ea8b96 | 616235514d65b822291e24d80df126c1e4bd115c2e4fc6cf16de0cb196278e81 | c1ccccc1 | C-N(-C)-C(=O)-[S;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[SH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A mixture of (3-dimethylcarbamoylsulfanyl-phenyl)-acetic acid methyl ester (2.0 g., 7.9 mmol), potassium hydroxide (1.4 g, 24 mmol),methanol (50 mL), and water (5 mL) is stirred at reflux 3 hr. The mixture is concentrated, and product partitioned between 1M aqueous hydrochloric acid (50 mL) and ethyl acetate (3×75 mL).... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Monosulfide | Aromatic thiol | null | null | c1ccccc1 | HO- | O | null | null | COC(=O)Cc1cccc(SC(=O)N(C)C)c1>O>COC(=O)Cc1cccc(S)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0ddd15bd71be493e9ebe30c4f7a0404b | C=CC(=O)OC.COC(=O)c1ccc(Br)c(C)c1>>COC(=O)C=Cc1ccc(CO)cc1C | COC(C1=CC(=C(C=C1)Br)C)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].COC(C=C)=O.C1(=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)C.C(C)(C)N(C(C)C)CC>>COC(C=CC1=C(C=C(C=C1)CO)C)=O | [CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH2:6].CO[C:11]([c:10]1[cH:9][cH:8][c:7](Br)[c:14]([CH3:15])[cH:13]1)=[O:12]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][OH:12])[cH:13][c:14]1[CH3:15] | C=CC(=O)OC.COC(=O)c1ccc(Br)c(C)c1 | COC(=O)C=Cc1ccc(CO)cc1C | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | O1CCCC1 | C-C Coupling | OtherReaction | 7d86193405b48fb76ba9dcee37063cf33cd92a496434813a875fc9de07673ba3 | 39869bba07b90fb136399f279c0b7c0111633ac4f08ff389480b9e60de8b1c4d | c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](-[C;H0;D3;+0:5](=[O;H0;D1;+0:6])-O-C):[c:7]:[c:8]:1-[C;D1;H3:9].[C;D1;H3:10]-[#8:11]-[C:12](=[O;D1;H0:13])-[C:14]=[CH2;D1;+0:15]>>[C;D1;H3:9]-[c:8]1:[c:7]:[c:4](-[CH2;D2;+0:5]-[OH;D1;+0:6]):[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[CH;D2;+0:15]=[C:14]-[C:12](=[O;D1;H0:13])-[#8:11]-[C;D1;H3:10] | null | [] | null | null | null | null | A mixture of methyl-4-bromo-3-methylbenzoate (5.7 g, 24.88 mmol), lithium aluminum hydride (29 mL, 29 mmol, 1 M solution in tetrahydrofuran) and tetrahydrofuran (100 mL) is stirred in ice/water for 1 hr. The reaction is quenched with aqueous hydrochloric acid (50 mL, 1 M). The product is extracted into ethyl acetate (3... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Vinyl | Primary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O1CCCC1 | null | null | C=CC(=O)OC.COC(=O)c1ccc(Br)c(C)c1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O1CCCC1>COC(=O)C=Cc1ccc(CO)cc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-476e396e96914fcbbcfc72384bc6a297 | COC(=O)C=Cc1ccc(CO)cc1C>>COC(=O)CCc1ccc(CO)cc1C | COC(C=CC1=C(C=C(C=C1)CO)C)=O.[H][H]>>COC(CCC1=C(C=C(C=C1)CO)C)=O | [CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][OH:12])[cH:13][c:14]1[CH3:15]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][OH:12])[cH:13][c:14]1[CH3:15] | COC(=O)C=Cc1ccc(CO)cc1C | COC(=O)CCc1ccc(CO)cc1C | null | [Ni] | O1CCCC1 | Reduction | Hydrogenation (double to single) | c04c38f95d7b746e5bdb99c368a7a33956c97b95b54c7ad89be2a85526386ec9 | 9a50abf8d2e4cd9195d7a0cadbe97483a261a81cf70b653cfddd5ecf76d383a6 | c1ccccc1 | [C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D2;+0:5]=[CH;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | null | null | null | null | A mixture of 3-(4-Hydroxymethyl-2-methyl-phenyl)-acrylic acid methyl ester (4.7 g, 22.8 mmol), Raney nickel (0.668 g) and tetrahydrofuran (618 mL) is shaken under 60 psig. Hydrogen 24 hr. The catalyst is filtered off, and the mixture is concentrated to afford the product as a pale yellow oil, 4.3 g, 91%. The structure ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | c1ccccc1 | null | [Ni].O1CCCC1 | null | null | COC(=O)C=Cc1ccc(CO)cc1C>[Ni].O1CCCC1>COC(=O)CCc1ccc(CO)cc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d6afd762fe934dcfaf80cf97406e3e8b | COC(=O)CCc1ccc(CO)cc1C.II>>COC(=O)CCc1ccc(CI)cc1C | COC(CCC1=C(C=C(C=C1)CO)C)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.ClCCl.II>>COC(CCC1=C(C=C(C=C1)CI)C)=O | O[CH2:11][c:10]1[cH:9][cH:8][c:7]([CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[c:14]([CH3:15])[cH:13]1.I[I:12]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][I:12])[cH:13][c:14]1[CH3:15] | COC(=O)CCc1ccc(CO)cc1C.II | COC(=O)CCc1ccc(CI)cc1C | null | null | S(=O)(O)[O-].[Na+].C1=CC=CC=C1 | Functional Group Interconversion | OtherReaction | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccccc1 | I-[I;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[I;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | A mixture of 3-(4-Hydroxymethyl-2-methyl-phenyl)-propionic acid methyl ester (0.62 g, 2.98 mmol), triphenyl phosphine (0.86 g, 3.27 mmol) and dichloromethane (10 mL) is stirred at room temperature. A solution of iodine (0.83 g, 3.27 mmol) in benzene (5 mL) is added and the black mixture is stirred at room temperature 2... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccccc1 | HI | S(=O)(O)[O-].[Na+].C1=CC=CC=C1 | null | null | COC(=O)CCc1ccc(CO)cc1C.II>S(=O)(O)[O-].[Na+].C1=CC=CC=C1>COC(=O)CCc1ccc(CI)cc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-96cb7506b94b438cbadc12c2572422eb | COC(=O)CBr.Cc1cc(Br)ccc1O>>COC(=O)COc1ccc(Br)cc1C | BrC1=CC(=C(C=C1)O)C.[H-].[Na+].CN(C=O)C.COC(CBr)=O>>COC(COC1=C(C=C(C=C1)Br)C)=O | Br[CH2:5][C:3]([O:2][CH3:1])=[O:4].[OH:6][c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][c:13]1[CH3:14]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][c:13]1[CH3:14] | COC(=O)CBr.Cc1cc(Br)ccc1O | COC(=O)COc1ccc(Br)cc1C | null | null | O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | null | null | 18 | HOUR | A mixture of 4-bromo-2-methylphenol (1.0 g, 5.35 mmol), sodium hydride (0.26 g, 6.42 mmol, 60% mineral oil), N,N-dimethylformamide (10 mL), and methyl-2-bromoacetate (0.56 mL, 5.88 mmol) is stirred at room temperature 18 hr. The mixture is diluted with water (50 mL) and the product extracted to ethyl acetate (3×50 mL).... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1 | HBr | O | null | 18 | COC(=O)CBr.Cc1cc(Br)ccc1O>O>COC(=O)COc1ccc(Br)cc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d9d4c8f34da04b73ae6b70991b0b57d6 | C=CC(=O)OC.Cc1cc([N+](=O)[O-])ccc1Br>>COC(=O)C=Cc1ccc([N+](=O)[O-])cc1C | C(C=C)(=O)OC.C1(=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)C.BrC1=C(C=C(C=C1)[N+](=O)[O-])C.CCN(C(C)C)C(C)C>>COC(C=CC1=C(C=C(C=C1)[N+](=O)[O-])C)=O | [CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH2:6].Br[c:7]1[cH:8][cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][c:15]1[CH3:16]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH:6][c:7]1[cH:8][cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][c:15]1[CH3:16] | C=CC(=O)OC.Cc1cc([N+](=O)[O-])ccc1Br | COC(=O)C=Cc1ccc([N+](=O)[O-])cc1C | null | CC(=O)[O-].CC(=O)[O-].[Pd+2] | C(CC)#N | C-C Coupling | Heck terminal vinyl | 55becfded1a3842d5a03bbf3e1610411c659aff0806930400c4db2ef61f9c87f | 4b186811a4930853b446d93d9faa39b267bddb9ce0b8021bda5c5a3b2bc69f0b | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6].[C;D1;H3:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[C:11]=[CH2;D1;+0:12]>>[C;D1;H3:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[CH;D2;+0:12]=[C:11]-[C:9](=[O;D1;H0:10])-[#8:8]-[C;D1;H3:7]):[c:2]:[c:3] | 91.1 | [{"value": 91.0, "product": "COC(C=CC1=C(C=C(C=C1)[N+](=O)[O-])C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.1, "product": "COC(C=CC1=C(C=C(C=C1)[N+](=O)[O-])C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | null | null | To a solution of 2-bromo-5-nitrotoluene (3.11 g, 14.39 mmol) in propionitrile (105 mL) is added DIPEA (5.1 mL, 29.28 mmol). The mixture is degassed three times. Methyl acrylate (5.2 mL, 57.74 mmol) is added and the mixture is degassed. Tri-o-tolylphosphine (1.77 g, 5.82 mmol) and Pd(OAc)2 (0.64 g, 2.85 mmol) are added ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)#N | 110 | null | C=CC(=O)OC.Cc1cc([N+](=O)[O-])ccc1Br>CC(=O)[O-].CC(=O)[O-].[Pd+2].C(CC)#N>COC(=O)C=Cc1ccc([N+](=O)[O-])cc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f0102356a8a14674ac1591db8b1e7720 | COC(=O)C=Cc1ccc([N+](=O)[O-])cc1C>>COC(=O)CCc1ccc(N)cc1C | COC(C=CC1=C(C=C(C=C1)[N+](=O)[O-])C)=O.[H][H]>>COC(CCC1=C(C=C(C=C1)N)C)=O | O=[N+:11]([O-])[c:10]1[cH:9][cH:8][c:7]([CH:6]=[CH:5][C:3]([O:2][CH3:1])=[O:4])[c:13]([CH3:14])[cH:12]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([NH2:11])[cH:12][c:13]1[CH3:14] | COC(=O)C=Cc1ccc([N+](=O)[O-])cc1C | COC(=O)CCc1ccc(N)cc1C | null | [Pd] | CO | Reduction | OtherReaction | 3f68c33e99a3b1d87eade4cb058e004f29cc4e463fd37ee2ca641c4da386de92 | 9a286a70d51062ea3254eea613fd78de0245b1fa6fc90a61d071cd4a0816e28b | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2]1:[c:3]:[c:4]:[c:5](-[CH;D2;+0:6]=[CH;D2;+0:7]-[C:8](=[O;D1;H0:9])-[#8:10]-[C;D1;H3:11]):[c:12]:[c:13]:1>>[C;D1;H3:11]-[#8:10]-[C:8](=[O;D1;H0:9])-[CH2;D2;+0:7]-[CH2;D2;+0:6]-[c:5]1:[c:4]:[c:3]:[c:2](-[NH2;D1;+0:1]):[c:13]:[c:12]:1 | 77.2 | [{"value": 77.0, "product": "COC(CCC1=C(C=C(C=C1)N)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.2, "product": "COC(CCC1=C(C=C(C=C1)N)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-(2-Methyl-4-nitro-phenyl)-acrylic acid methyl ester (1.47 g, 6.64 mmol) and 5% Pd/C (0.29 g) in MeOH (100 mL) is exposed to a hydrogen atmosphere (60 psi) for 12 h. The mixture is filtered through Celite and purified by flash chromatography to yield the title compound (0.99 g, 77%).
Conditions: See react... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Nitro group | Ester.Primary amine | null | null | c1ccccc1 | Other | [Pd].CO | null | null | COC(=O)C=Cc1ccc([N+](=O)[O-])cc1C>[Pd].CO>COC(=O)CCc1ccc(N)cc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cad4a9d701a44e44b207b23e6b398c43 | COC(=O)CCc1ccc(CO)cc1C>>COC(=O)CCc1ccc(C=O)cc1C | COC(CCC1=C(C=C(C=C1)CO)C)=O>>COC(CCC1=C(C=C(C=C1)C=O)C)=O | [CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][OH:12])[cH:13][c:14]1[CH3:15]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([CH:11]=[O:12])[cH:13][c:14]1[CH3:15] | COC(=O)CCc1ccc(CO)cc1C | COC(=O)CCc1ccc(C=O)cc1C | null | O=[Mn]=O | C(Cl)(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccccc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | 60 | [{"value": 60.0, "product": "COC(CCC1=C(C=C(C=C1)C=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | DAY | A mixture of 3-(4-Hydroxymethyl-2-methyl-phenyl)-propionic acid methyl ester (0.49 g, 2.35 mmol) and MnO2 (0.80 g, 9.20 mmol) in chloroform (5 mL) is stirred at RT for 4 days. The mixture is filtered through Celite; the Celite is washed with copious amounts of EtOAc. The filtrate is concentrated and purified by flash c... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1 | null | O=[Mn]=O.C(Cl)(Cl)Cl | null | 96 | COC(=O)CCc1ccc(CO)cc1C>O=[Mn]=O.C(Cl)(Cl)Cl>COC(=O)CCc1ccc(C=O)cc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7047c07b8f0142c6b8bef6053ad76cb2 | COC(=O)CCc1ccc(CO)cc1C.O=S(Cl)Cl>>COC(=O)CCc1ccc(CCl)cc1C | O.S(=O)(Cl)Cl.COC(CCC1=C(C=C(C=C1)CO)C)=O.C(C)N(CC)CC>>COC(CCC1=C(C=C(C=C1)CCl)C)=O | O[CH2:11][c:10]1[cH:9][cH:8][c:7]([CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[c:14]([CH3:15])[cH:13]1.O=S(Cl)[Cl:12]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][Cl:12])[cH:13][c:14]1[CH3:15] | COC(=O)CCc1ccc(CO)cc1C.O=S(Cl)Cl | COC(=O)CCc1ccc(CCl)cc1C | null | null | C(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_SOCl2 | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[Cl;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 91 | [{"value": 91.0, "product": "COC(CCC1=C(C=C(C=C1)CCl)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.9, "product": "COC(CCC1=C(C=C(C=C1)CCl)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a 0° C. solution of 3-(4-Hydroxymethyl-2-methyl-phenyl)-propionic acid methyl ester (1.02 g, 4.90 mmol) in anhydrous CH2Cl2 (15 mL) is added triethylamine (0.75 mL, 5.38 mmol) followed by thionyl chloride (0.40 mL, 5.48 mmol). The mixture is allowed to warm to RT overnight. Water is added, and the mixture is extract... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccccc1 | HCl | C(Cl)Cl | null | null | COC(=O)CCc1ccc(CO)cc1C.O=S(Cl)Cl>C(Cl)Cl>COC(=O)CCc1ccc(CCl)cc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8d3e76129ce74d6693bb187128c35d37 | COC(=O)CCc1ccc(CCl)cc1C.[N-]=[N+]=[N-]>>COC(=O)CCc1ccc(CN=[N+]=[N-])cc1C | O.COC(CCC1=C(C=C(C=C1)CCl)C)=O.[N-]=[N+]=[N-].[Na+]>>COC(CCC1=C(C=C(C=C1)CN=[N+]=[N-])C)=O | Cl[CH2:11][c:10]1[cH:9][cH:8][c:7]([CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[c:16]([CH3:17])[cH:15]1.[N-:12]=[N+:13]=[N-:14]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][N:12]=[N+:13]=[N-:14])[cH:15][c:16]1[CH3:17] | COC(=O)CCc1ccc(CCl)cc1C.[N-]=[N+]=[N-] | COC(=O)CCc1ccc(CN=[N+]=[N-])cc1C | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 4b07a4c2a14d792a37e78a751619e60b15c60cbff0bebae1109754fb52d84cbb | 2d41632f7225d65cdc2ad8562dfb28f3f5a017f92040ed4ccafbb8154954c8fe | c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[N-;H0;D1:5]=[#7;+:6]=[N;-;D1;H0:7]>>[N;-;D1;H0:7]=[#7;+:6]=[N;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 91 | [{"value": 91.0, "product": "COC(CCC1=C(C=C(C=C1)CN=[N+]=[N-])C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.9, "product": "COC(CCC1=C(C=C(C=C1)CN=[N+]=[N-])C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 3-(4-Chloromethyl-2-methyl-phenyl)-propionic acid methyl ester (0.52 g, 2.31 mmol) in DMF (7 mL) is added sodium azide (0.25 g, 3.84 mmol). The mixture is stirred overnight. Water is added, and the mixture is extracted with EtOAc. The organics are dried with Na2SO4 and concentrated to yield the title c... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Azide | null | null | c1ccccc1 | Other | CN(C)C=O | null | 8 | COC(=O)CCc1ccc(CCl)cc1C.[N-]=[N+]=[N-]>CN(C)C=O>COC(=O)CCc1ccc(CN=[N+]=[N-])cc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-94a6019a1fd24619b8cf383a7ae1c3be | COC(=O)CCc1ccc(CN=[N+]=[N-])cc1C>>COC(=O)CCc1ccc(CN)cc1C | COC(CCC1=C(C=C(C=C1)CN=[N+]=[N-])C)=O.[H][H]>>COC(CCC1=C(C=C(C=C1)CN)C)=O | [N-]=[N+]=[N:12][CH2:11][c:10]1[cH:9][cH:8][c:7]([CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[c:14]([CH3:15])[cH:13]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][NH2:12])[cH:13][c:14]1[CH3:15] | COC(=O)CCc1ccc(CN=[N+]=[N-])cc1C | COC(=O)CCc1ccc(CN)cc1C | null | [Pd] | CCO | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | c1ccccc1 | [N-]=[N+]=[N;H0;D2;+0:1]-[C:2]-[c:3]>>[NH2;D1;+0:1]-[C:2]-[c:3] | 78.5 | [{"value": 78.0, "product": "COC(CCC1=C(C=C(C=C1)CN)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.5, "product": "COC(CCC1=C(C=C(C=C1)CN)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-(4-Azidomethyl-2-methyl-phenyl)-propionic acid methyl ester (0.20 g, 0.86 mmol) and 5% Pd/C (32 mg) in EtOH (50 mL) is exposed to a hydrogen atmosphere (60 psi) at RT overnight. Upon filtering the mixture through Celite, the filtrate is concentrated to yield the title compound (0.14 g, 78%). The material... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | c1ccccc1 | Other | [Pd].CCO | null | null | COC(=O)CCc1ccc(CN=[N+]=[N-])cc1C>[Pd].CCO>COC(=O)CCc1ccc(CN)cc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d9b5e75adf0e48869f9a9fff941b564e | O=Cc1ccc(-c2ccc(C(F)(F)F)cc2)s1>>OCc1ccc(-c2ccc(C(F)(F)F)cc2)s1 | FC(C1=CC=C(C=C1)C1=CC=C(S1)C=O)(F)F.[Li+].[BH4-]>>FC(C1=CC=C(C=C1)C1=CC=C(S1)CO)(F)F | [O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]2)[s:17]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]2)[s:17]1 | O=Cc1ccc(-c2ccc(C(F)(F)F)cc2)s1 | OCc1ccc(-c2ccc(C(F)(F)F)cc2)s1 | null | null | C1CCOC1 | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccc(-c2cccs2)cc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[#16;a:5]:[c:6]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[#16;a:5]:[c:6] | null | [] | null | null | 15 | MINUTE | To a solution of 5-(4-Trifluoromethyl-phenyl)-thiophene-2-carbaldehyde (3.02 g, 11.8 mmole) in THF (100 mL), is added to LiBH4 (1.75 g, 80.24 mmole) in one portion at 0° C. The reaction is kept at 0° C. for 15 minutes and warmed up to room temperature for 1 hour. The reaction is quenched using 5N HCl (100 mL) at 0° C. ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccsc1.c1ccccc1 | null | C1CCOC1 | null | 0.25 | O=Cc1ccc(-c2ccc(C(F)(F)F)cc2)s1>C1CCOC1>OCc1ccc(-c2ccc(C(F)(F)F)cc2)s1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-98d68cde2bec498d802059a64c64ffde | CS(=O)(=O)Cl.OCc1ccc(-c2ccc(C(F)(F)F)cc2)s1>>FC(F)(F)c1ccc(-c2ccc(CCl)s2)cc1 | FC(C1=CC=C(C=C1)C1=CC=C(S1)CO)(F)F.C(C)N(CC)CC.CS(=O)(=O)Cl>>ClCC=1SC(=CC1)C1=CC=C(C=C1)C(F)(F)F | CS(=O)(=O)[Cl:14].O[CH2:13][c:12]1[cH:11][cH:10][c:9](-[c:8]2[cH:7][cH:6][c:5]([C:2]([F:1])([F:3])[F:4])[cH:17][cH:16]2)[s:15]1>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([CH2:13][Cl:14])[s:15]2)[cH:16][cH:17]1 | CS(=O)(=O)Cl.OCc1ccc(-c2ccc(C(F)(F)F)cc2)s1 | FC(F)(F)c1ccc(-c2ccc(CCl)s2)cc1 | null | null | C(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_sulfonyl chloride | 58d25ddf86b8daa38762ecb08ed922faa2d01716f69924f9b8413703fe1b3fc7 | d5d71bad4297b1f4f93dd1d1d9cddf0bb6fadb3f4dca1f84369c4074a39097d6 | c1ccc(-c2cccs2)cc1 | C-S(=O)(=O)-[Cl;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3](:[c:4]):[#16;a:5]:[c:6]>>[Cl;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[#16;a:5]:[c:6] | null | [] | null | null | null | null | To a mixture of [5-(4-Trifluoromethyl-phenyl)-thiophen-2-yl]-methanol (1.52 g, 5.89 mmole) and triethyl amine (1.64 mL, 11.78 mmole) in DCM (100 mL) at 0° C., is injected methanesulfonyl chloride (0.91 mL, 11.78 mmole) dropwise. The reaction is kept at 0° C. for an hour and warmed up to room temperature for an hour. Th... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Primary halide | null | null | c1ccccc1.c1ccsc1 | HO- | C(Cl)Cl | null | null | CS(=O)(=O)Cl.OCc1ccc(-c2ccc(C(F)(F)F)cc2)s1>C(Cl)Cl>FC(F)(F)c1ccc(-c2ccc(CCl)s2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c916ec0ec8ff497f8a532ebae68c5e0d | CI.O=Cc1ccc(-c2ccc(C(F)(F)F)cc2)s1>>Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O | CNCCN(C)C.FC(C1=CC=C(C=C1)C1=CC=C(S1)C=O)(F)F.C(CCC)[Li].C1CCCCC1.C1CCCCC1.IC.C(CCC)[Li]>>CC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C=O | I[CH3:1].[cH:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]2)[s:15][c:16]1[CH:17]=[O:18]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]2)[s:15][c:16]1[CH:17]=[O:18] | CI.O=Cc1ccc(-c2ccc(C(F)(F)F)cc2)s1 | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O | null | null | C1CCOC1 | C-C Coupling | Methylation with MeI_aryl | 7e15613f3c958c40dd77c6dbedcc2b00a5239879ab7fa778e50231e6a36333de | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | c1ccc(-c2cccs2)cc1 | I-[CH3;D1;+0:1].[O;D1;H0:2]=[C:3]-[c:4]1:[#16;a:5]:[c:6](-[c:7]):[c:8]:[cH;D2;+0:9]:1>>[CH3;D1;+0:1]-[c;H0;D3;+0:9]1:[c:8]:[c:6](-[c:7]):[#16;a:5]:[c:4]:1-[C:3]=[O;D1;H0:2] | null | [] | -18 | CELSIUS | 15 | MINUTE | To a solution of trimethylethylenediamine (0.296 mL, 2.28 mmole) in THF at −78° C., is injected 2.0M n-butyllithium in cyclohexane (1.14 mL, 2.28 mmole) dropwise. The mixture is stirred for 15 minutes, then added a solution of 5-(4-Trifluoromethyl-phenyl)-thiophene-2-carbaldehyde (0.530 g, 2.07 mmole) in THF (5 mL) and... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccsc1 | c1ccsc1 | c1ccsc1.c1ccccc1 | HI | C1CCOC1 | -18 | 0.25 | CI.O=Cc1ccc(-c2ccc(C(F)(F)F)cc2)s1>C1CCOC1>Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f2d6a7054a7142a989ab67dc32fa753b | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O>>OCc1ccc(-c2ccc(C(F)(F)F)cc2)s1 | CC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C=O.[Li+].[BH4-]>>FC(C1=CC=C(C=C1)C1=CC=C(S1)CO)(F)F | C[c:4]1[c:3]([CH:2]=[O:1])[s:17][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]2)[cH:5]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]2)[s:17]1 | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O | OCc1ccc(-c2ccc(C(F)(F)F)cc2)s1 | null | null | C1CCOC1 | Miscellaneous | OtherReaction | ebb547296a6d21281419ae74f504700fd5978d3bc2d0351e2390b1a0c8bd00f3 | 43cf4997d6e2488d8c69ca8bc684124ace6515563d3e08dcc47ef2a56dd17cc0 | c1ccc(-c2cccs2)cc1 | C-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#16;a:5]:[c:6]:1-[CH;D2;+0:7]=[O;H0;D1;+0:8]>>[OH;D1;+0:8]-[CH2;D2;+0:7]-[c:6]1:[#16;a:5]:[c:3](-[c:4]):[c:2]:[cH;D2;+0:1]:1 | null | [] | null | null | 15 | MINUTE | To a solution of 3-methyl-5-(4-Trifluoromethyl-phenyl)-thiophene-2-carbaldehyde (0.140 g, 0.518 mmole) in THF (5 mL), is added to LiBH4 (0.056 g, 2.57 mmole) in one portion at 0° C. The reaction is kept at 0° C. for 15 minutes and warmed up to room temperature for 1 hour. The reaction is quenched using 1N HCl (10 mL) a... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | c1ccsc1 | c1ccsc1 | c1ccsc1.c1ccccc1 | Other | C1CCOC1 | null | 0.25 | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O>C1CCOC1>OCc1ccc(-c2ccc(C(F)(F)F)cc2)s1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-acb9feedec8c49e6b9950982176e97e0 | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O>>Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(C)O | CC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C=O.C[Mg+].[Br-].C(C)OCC>>CC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(C)O | [CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]2)[s:15][c:16]1[CH:17]=[O:19]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]2)[s:15][c:16]1[CH:17]([CH3:18])[OH:19] | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(C)O | null | null | C1CCOC1 | Miscellaneous | OtherReaction | 1ffaf80f172e20da969364a5d2977299bc51b204f2262675c45c8ec58ff36ac0 | e005d650d08e61fc67b766830eb53235a9bc084cc3667d2f8a73c2fb8bb34277 | c1ccc(-c2cccs2)cc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[#16;a:5]:[c:6]>>[C;D1;H3:7]-[CH;D3;+0:2](-[OH;D1;+0:1])-[c:3](:[c:4]):[#16;a:5]:[c:6] | null | [] | null | null | 2 | HOUR | To a solution of 3-methyl-5-(4-Trifluoromethyl-phenyl)-thiophene-2-carbaldehyde (0.130 g, 0.481 mmole) in THF (5 mL), is injected 3.0 M MeMgBr in ethyl ether (0.27 mL, 0.810 mmole) dropwise. The reaction is stirred for 2 hours. The reaction is quenched with saturated NH4Cl(aq) (10 mL), then the aqueous solution is extr... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol | null | null | c1ccsc1.c1ccccc1 | Other | C1CCOC1 | null | 2 | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O>C1CCOC1>Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(C)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ad8501f194484cd9ad4078268feb9f9f | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O>>O=Cc1sc(-c2ccc(C(F)(F)F)cc2)cc1B(O)O | FC(C1=CC=C(C=C1)C1=CC=C(S1)C=O)(F)F.B(OC)(OC)OC.CC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C=O>>C(=O)C=1SC(=CC1B(O)O)C1=CC=C(C=C1)C(F)(F)F | C[c:17]1[c:3]([CH:2]=[O:1])[s:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[cH:16]1>>[O:1]=[CH:2][c:3]1[s:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[cH:16][c:17]1[B:18]([OH:19])[OH:20] | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O | O=Cc1sc(-c2ccc(C(F)(F)F)cc2)cc1B(O)O | null | null | null | Functional Group Interconversion | OtherReaction | 58706035a185404c007ec1ac6b6d9048358b567fabc911e2e9026aab27cdd8a4 | d6d312d46f766d2774f96de1fd96fd8f98a20e51a20ef3280f850cd6a3c77869 | c1ccc(-c2cccs2)cc1 | C-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#16;a:5]:[c:6]:1-[C:7]=[O;D1;H0:8]>>[O;D1;H0:8]=[C:7]-[c:6]1:[#16;a:5]:[c:3](-[c:4]):[c:2]:[c;H0;D3;+0:1]:1-[#5:9](-[O;D1;H1:10])-[O;D1;H1:11] | null | [] | null | null | null | null | The titled compound is prepared from 5-(4-Trifluoromethyl-phenyl)-thiophene-2-carbaldehyde (2.70 g, 10 mmole) and trimethyl borate (5.68 g, 50.0 mmole) in a similar manner to 3-Methyl-5-(4-trifluoromethyl-phenyl)-thiophene-2-carbaldehyde.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | Boronic acid | c1ccsc1 | c1ccsc1 | c1ccsc1.c1ccccc1 | null | null | null | null | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O>>O=Cc1sc(-c2ccc(C(F)(F)F)cc2)cc1B(O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6405b8ad43a24f0890e4f7cae16c7d57 | C=C(C)Br.O=Cc1sc(-c2ccc(C(F)(F)F)cc2)cc1B(O)O>>C=C(C)c1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O | C(=O)C=1SC(=CC1B(O)O)C1=CC=C(C=C1)C(F)(F)F.BrC(=C)C.[F-].[Cs+]>>C(=C)(C)C1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C=O | Br[C:2](=[CH2:1])[CH3:3].OB(O)[c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]2)[s:17][c:18]1[CH:19]=[O:20]>>[CH2:1]=[C:2]([CH3:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]2)[s:17][c:18]1[CH:19]=[O:20] | C=C(C)Br.O=Cc1sc(-c2ccc(C(F)(F)F)cc2)cc1B(O)O | C=C(C)c1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O | null | null | O1CCOCC1 | C-C Coupling | Suzuki coupling with boronic acids | a5bc9d8790fe7ff83d747557e3fc5ca989fb53f4eff2bed004045e1fedbd7fac | a1e0cb00430befa5863b57b017e611f2a9019384748c263482d05f7da8c611e2 | c1ccc(-c2cccs2)cc1 | Br-[C;H0;D3;+0:1](=[C;D1;H2:2])-[C;D1;H3:3].O-B(-O)-[c;H0;D3;+0:4]1:[c:5]:[c:6](-[c:7]):[#16;a:8]:[c:9]:1-[C:10]=[O;D1;H0:11]>>[C;D1;H2:2]=[C;H0;D3;+0:1](-[C;D1;H3:3])-[c;H0;D3;+0:4]1:[c:5]:[c:6](-[c:7]):[#16;a:8]:[c:9]:1-[C:10]=[O;D1;H0:11] | null | [] | null | null | null | null | To a mixture of 2-Formyl-5-(4-trifluoromethyl-phenyl)-thiophene-3-boronic acid (0.330 g, 1.10 mmole), 2-Bromo-propene (0.399 g, 3.30 mmole) and cesium fluoride (0.585 g, 3.85 mmole) in dioxane (5 mL), is bubbled with nitrogen gas for 15 minutes. The catalyst PdCl2 (dppf) (0.033 g) is then added to the mixture. The reac... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Boronic acid | Vinyl | c1ccsc1 | c1ccsc1 | c1ccsc1.c1ccccc1 | HBr.B | O1CCOCC1 | null | null | C=C(C)Br.O=Cc1sc(-c2ccc(C(F)(F)F)cc2)cc1B(O)O>O1CCOCC1>C=C(C)c1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e70bee66491d4194abaaf67ed0f9b594 | C=C(C)c1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O>>C=C(C)c1cc(-c2ccc(C(F)(F)F)cc2)sc1CO | C(=C)(C)C1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C=O.[BH4-].[Na+]>>C(=C)(C)C1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)CO | [CH2:1]=[C:2]([CH3:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]2)[s:17][c:18]1[CH:19]=[O:20]>>[CH2:1]=[C:2]([CH3:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]2)[s:17][c:18]1[CH2:19][OH:20] | C=C(C)c1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O | C=C(C)c1cc(-c2ccc(C(F)(F)F)cc2)sc1CO | null | null | C1CCOC1 | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccc(-c2cccs2)cc1 | [C;D1;H2:1]=[C:2]-[c:3]:[c:4](-[CH;D2;+0:5]=[O;H0;D1;+0:6]):[#16;a:7]:[c:8]>>[C;D1;H2:1]=[C:2]-[c:3]:[c:4](-[CH2;D2;+0:5]-[OH;D1;+0:6]):[#16;a:7]:[c:8] | null | [] | null | null | 15 | MINUTE | To a solution of 3-Isopropenyl-5-(4-trifluoromethyl-phenyl)-thiophene-2-carbaldehyde (0.084 g, 0.283 mmole) in THF (3 mL), is added to NaBH4 (0.023 g, 0.622 mmole) in one portion at 0° C. The reaction is kept at 0° C. for 15 minutes and warmed up to room temperature for 2 hours. The reaction is quenched using saturated... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccsc1.c1ccccc1 | null | C1CCOC1 | null | 0.25 | C=C(C)c1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O>C1CCOC1>C=C(C)c1cc(-c2ccc(C(F)(F)F)cc2)sc1CO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c911797e2cd04532ac685195fda962e8 | C=C(C)c1cc(-c2ccc(C(F)(F)F)cc2)sc1CO>>CC(C)c1cc(-c2ccc(C(F)(F)F)cc2)sc1CO | C(=C)(C)C1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)CO>>C(C)(C)C1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)CO | [CH2:1]=[C:2]([CH3:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]2)[s:17][c:18]1[CH2:19][OH:20]>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]2)[s:17][c:18]1[CH2:19][OH:20] | C=C(C)c1cc(-c2ccc(C(F)(F)F)cc2)sc1CO | CC(C)c1cc(-c2ccc(C(F)(F)F)cc2)sc1CO | null | [Pd] | null | Reduction | Hydrogenation (double to single) | 8276b4fb5ddc7d15dec6d92474e91e2dbb2fb8b81e5b5720762e5d89cb27aa69 | 1ccae9f2e86499601fc3421041ff4588c8e6fd53048e86c3b6ed12ae873609c0 | c1ccc(-c2cccs2)cc1 | [C:1]-[c:2]1:[#16;a:3]:[c:4]:[c:5]:[c:6]:1-[C;H0;D3;+0:7](-[C;D1;H3:8])=[CH2;D1;+0:9]>>[C:1]-[c:2]1:[#16;a:3]:[c:4]:[c:5]:[c:6]:1-[CH;D3;+0:7](-[C;D1;H3:8])-[CH3;D1;+0:9] | null | [] | null | null | null | null | The solution of [3-Isopropenyl-5-(4-trifluoromethyl-phenyl)-thiophen-2-yl]-methanol (0.084 g, 0.282 mmole) is stirred under nitrogen gas in presence of 10% palladium on carbon (0.085 g) for 16 hours. The catalyst is removed by filtration, and the filtrate is concentrated to provide the titled compound as white solid, w... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | null | null | null | c1ccsc1.c1ccccc1 | null | [Pd] | null | null | C=C(C)c1cc(-c2ccc(C(F)(F)F)cc2)sc1CO>[Pd]>CC(C)c1cc(-c2ccc(C(F)(F)F)cc2)sc1CO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-256a6fe14b94461bbcd1ace5552bb17f | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(C)O>>CC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1C | CC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(C)O>>CC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(C)=O | [CH3:1][CH:2]([OH:3])[c:4]1[s:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]2)[cH:17][c:18]1[CH3:19]>>[CH3:1][C:2](=[O:3])[c:4]1[s:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]2)[cH:17][c:18]1[CH3:19] | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(C)O | CC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1C | null | O=[Mn]=O.O=[Mn]=O | null | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | c1ccc(-c2cccs2)cc1 | [C;D1;H3:1]-[CH;D3;+0:2](-[OH;D1;+0:3])-[c:4](:[c:5]):[#16;a:6]:[c:7]>>[C;D1;H3:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4](:[c:5]):[#16;a:6]:[c:7] | null | [] | null | null | null | null | To a solution of 1-[3-Methyl-5-(4-trifluoromethyl-phenyl)-thiophen-2-yl]-ethanol (see Preparation 8) (4.40 g, 15.4 mmole), is added MnO2 (7.88 g, 77.0 mmole) in one portion. The mixture is heated under reflux for 16 hours, more MnO2 (7.88 g, 77.0 mmole) is added to the reaction and continued to reflux for 4 hours. The ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1ccsc1.c1ccccc1 | null | O=[Mn]=O.O=[Mn]=O | null | null | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(C)O>O=[Mn]=O.O=[Mn]=O>CC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-94344deaed9e46efa33b12f492d2e270 | CC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1C.COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1>>COC=C(C)c1sc(-c2ccc(C(F)(F)F)cc2)cc1C | CC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(C)=O.[Cl-].COC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CC(C)([O-])C.[K+]>>COC=C(C)C=1SC(=CC1C)C1=CC=C(C=C1)C(F)(F)F | O=[C:4]([CH3:5])[c:6]1[s:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][cH:18]2)[cH:19][c:20]1[CH3:21].c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:3][O:2][CH3:1])cc1>>[CH3:1][O:2][CH:3]=[C:4]([CH3:5])[c:6]1[s:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][cH:18]2)[cH:19][c:20]... | CC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1C.COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1 | COC=C(C)c1sc(-c2ccc(C(F)(F)F)cc2)cc1C | null | null | C1(=CC=CC=C1)C.C1CCOC1 | C-C Coupling | Wittig with Phosphonium | 183135d5dbdf71ecf3df8474088b3eff5f51c5ed39d27c562953dba9cee5701e | bc49b37cfad095ef21edb56cfe703ef15fa2ade769431a305bbc0346ae1ffa96 | c1ccc(-c2cccs2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[#16;a:5]:[c:6].[C;D1;H3:7]-[#8:8]-[CH2;D2;+0:9]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C;D1;H3:7]-[#8:8]-[CH;D2;+0:9]=[C;H0;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[#16;a:5]:[c:6] | null | [] | null | null | 30 | MINUTE | To a solution of (methoxymethyl)triphenyl phosphonium chloride (3.96 g, 10.76 mmole) in toluene/THF (2:1, 60 mL), is added potassium t-butoxide (1.21 g, 10.76 mmole) in one portion and stirred for 30 minutes. To the resulting ylide, is injected into a solution of 1-[3-Methyl-5-(4-trifluoromethyl-phenyl)-thiophen-2-yl]-... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether | Ether | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccsc1.c1ccccc1 | HO- | C1(=CC=CC=C1)C.C1CCOC1 | null | 0.5 | CC(=O)c1sc(-c2ccc(C(F)(F)F)cc2)cc1C.COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1>C1(=CC=CC=C1)C.C1CCOC1>COC=C(C)c1sc(-c2ccc(C(F)(F)F)cc2)cc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a1f6a4333a694a84bfcc046a232e3074 | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(C)C=O>>Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(C)CO | CC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(C=O)C.[BH4-].[Na+]>>CC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(CO)C | [CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]2)[s:15][c:16]1[CH:17]([CH3:18])[CH:19]=[O:20]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]2)[s:15][c:16]1[CH:17]([CH3:18])[CH2:19][OH:20] | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(C)C=O | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(C)CO | null | null | C1CCOC1 | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccc(-c2cccs2)cc1 | [#16;a:1]:[c:2]-[C:3](-[C;D1;H3:4])-[CH;D2;+0:5]=[O;H0;D1;+0:6]>>[#16;a:1]:[c:2]-[C:3](-[C;D1;H3:4])-[CH2;D2;+0:5]-[OH;D1;+0:6] | null | [] | null | null | 15 | MINUTE | To a solution of 2-[3-Methyl-5-(4-trifluoromethyl-phenyl)-thiophen-2-yl]-propionaldehyde (1.40 g, 4.69 mmole) in THF (20 mL), is added to NaBH4 (0.266 g, 7.04 mmole) in one portion at 0° C. The reaction is kept at 0° C. for 15 minutes and warmed up to room temperature for 2 hours. The reaction is quenched using NH4Cl(a... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccsc1.c1ccccc1 | null | C1CCOC1 | null | 0.25 | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(C)C=O>C1CCOC1>Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(C)CO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dfee3024901a41058eca4305c84c80f0 | CC(=O)c1cc(-c2ccccc2)sc1C>>Cc1sc(-c2ccccc2)cc1C(C)O | CC=1SC(=CC1C(C)=O)C1=CC=CC=C1.[Li+].[BH4-]>>CC=1SC(=CC1C(C)O)C1=CC=CC=C1 | [CH3:1][c:2]1[s:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[cH:11][c:12]1[C:13]([CH3:14])=[O:15]>>[CH3:1][c:2]1[s:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[cH:11][c:12]1[CH:13]([CH3:14])[OH:15] | CC(=O)c1cc(-c2ccccc2)sc1C | Cc1sc(-c2ccccc2)cc1C(C)O | null | null | C1CCOC1 | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(-c2cccs2)cc1 | [C;D1;H3:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4]1:[c:5]:[c:6]:[#16;a:7]:[c:8]:1-[C;D1;H3:9]>>[C;D1;H3:1]-[CH;D3;+0:2](-[OH;D1;+0:3])-[c:4]1:[c:5]:[c:6]:[#16;a:7]:[c:8]:1-[C;D1;H3:9] | null | [] | null | null | 30 | MINUTE | To a solution of 1-(2-Methyl-5-phenyl-thiophen-3-yl)-ethanone (1.08 g, 5.00 mmole) in THF (20 mL), is added to LiBH4 (0.327 g, 15.0 mmole) in one portion at 0° C. The reaction is kept at 0° C. for 30 minutes and warmed up to room temperature for 2 hours. The reaction is quenched using NH4Cl(aq) (50 mL) at 0° C. The THF... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccsc1.c1ccccc1 | null | C1CCOC1 | null | 0.5 | CC(=O)c1cc(-c2ccccc2)sc1C>C1CCOC1>Cc1sc(-c2ccccc2)cc1C(C)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6c3090dad9ce47efa1756af0259d6d3c | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O>>Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(C)O | CC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C=O.C[Mg+].[Br-].C(C)OCC>>CC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C(C)O | [CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]2)[s:15][c:16]1[CH:17]=[O:19]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]2)[s:15][c:16]1[CH:17]([CH3:18])[OH:19] | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(C)O | null | null | C1CCOC1 | Miscellaneous | OtherReaction | 1ffaf80f172e20da969364a5d2977299bc51b204f2262675c45c8ec58ff36ac0 | e005d650d08e61fc67b766830eb53235a9bc084cc3667d2f8a73c2fb8bb34277 | c1ccc(-c2cccs2)cc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[#16;a:5]:[c:6]>>[C;D1;H3:7]-[CH;D3;+0:2](-[OH;D1;+0:1])-[c:3](:[c:4]):[#16;a:5]:[c:6] | null | [] | null | null | 2 | HOUR | To a solution of 3-methyl-5-(4-Trifluoromethyl-phenyl)-thiophene-2-carbaldehyde (0.130 g, 0.481 mmole) in THF (5 mL), is injected 3.0 M MeMgBr in ethyl ether (0.27 mL, 0.810 mmole) dropwise. The reaction is stirred for 2 hours. The reaction is quenched with saturated NH4Cl(aq) (10 mL), then the aqueous solution is extr... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Secondary alcohol | null | null | c1ccsc1.c1ccccc1 | Other | C1CCOC1 | null | 2 | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O>C1CCOC1>Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C(C)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7afae79c9f224155b1e94c00ac1c4ebc | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O>>O=Cc1sc(-c2ccc(C(F)(F)F)cc2)cc1B(O)O | FC(C1=CC=C(C=C1)C1=CC=C(S1)C=O)(F)F.B(OC)(OC)OC.CC1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C=O>>C(=O)C=1SC(=CC1B(O)O)C1=CC=C(C=C1)C(F)(F)F | C[c:17]1[c:3]([CH:2]=[O:1])[s:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[cH:16]1>>[O:1]=[CH:2][c:3]1[s:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[cH:16][c:17]1[B:18]([OH:19])[OH:20] | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O | O=Cc1sc(-c2ccc(C(F)(F)F)cc2)cc1B(O)O | null | null | null | Functional Group Interconversion | OtherReaction | 58706035a185404c007ec1ac6b6d9048358b567fabc911e2e9026aab27cdd8a4 | d6d312d46f766d2774f96de1fd96fd8f98a20e51a20ef3280f850cd6a3c77869 | c1ccc(-c2cccs2)cc1 | C-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#16;a:5]:[c:6]:1-[C:7]=[O;D1;H0:8]>>[O;D1;H0:8]=[C:7]-[c:6]1:[#16;a:5]:[c:3](-[c:4]):[c:2]:[c;H0;D3;+0:1]:1-[#5:9](-[O;D1;H1:10])-[O;D1;H1:11] | null | [] | null | null | null | null | The titled compound is prepared from 5-(4-Trifluoromethyl-phenyl)-thiophene-2-carbaldehyde (2.70 g, 10 mmole) and trimethyl borate (5.68 g, 50.0 mmole) in a similar manner to 3-Methyl-5-(4-trifluoromethyl-phenyl)-thiophene-2-carbaldehyde (Preparation 2, Step A).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | Boronic acid | c1ccsc1 | c1ccsc1 | c1ccsc1.c1ccccc1 | null | null | null | null | Cc1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O>>O=Cc1sc(-c2ccc(C(F)(F)F)cc2)cc1B(O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-15886303a1aa47449c61af5641936167 | C=C(C)Br.O=Cc1sc(-c2ccc(C(F)(F)F)cc2)cc1B(O)O>>C=C(C)c1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O | C(=O)C=1SC(=CC1B(O)O)C1=CC=C(C=C1)C(F)(F)F.BrC(=C)C.[F-].[Cs+]>>C(=C)(C)C1=C(SC(=C1)C1=CC=C(C=C1)C(F)(F)F)C=O | Br[C:2](=[CH2:1])[CH3:3].OB(O)[c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]2)[s:17][c:18]1[CH:19]=[O:20]>>[CH2:1]=[C:2]([CH3:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]2)[s:17][c:18]1[CH:19]=[O:20] | C=C(C)Br.O=Cc1sc(-c2ccc(C(F)(F)F)cc2)cc1B(O)O | C=C(C)c1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O | null | null | O1CCOCC1 | C-C Coupling | Suzuki coupling with boronic acids | a5bc9d8790fe7ff83d747557e3fc5ca989fb53f4eff2bed004045e1fedbd7fac | a1e0cb00430befa5863b57b017e611f2a9019384748c263482d05f7da8c611e2 | c1ccc(-c2cccs2)cc1 | Br-[C;H0;D3;+0:1](=[C;D1;H2:2])-[C;D1;H3:3].O-B(-O)-[c;H0;D3;+0:4]1:[c:5]:[c:6](-[c:7]):[#16;a:8]:[c:9]:1-[C:10]=[O;D1;H0:11]>>[C;D1;H2:2]=[C;H0;D3;+0:1](-[C;D1;H3:3])-[c;H0;D3;+0:4]1:[c:5]:[c:6](-[c:7]):[#16;a:8]:[c:9]:1-[C:10]=[O;D1;H0:11] | null | [] | null | null | null | null | To a mixture of 2-Formyl-5-(4-trifluoromethyl-phenyl)-thiophene-3-boronic acid (0.330 g, 1.10 mmole), 2-Bromo-propene (0.399 g, 3.30 mmole) and cesium fluoride (0.585 g, 3.85 mmole) in dioxane (5 mL), is bubbled with nitrogen gas for 15 minutes. The catalyst PdCl2 (dppf) (0.033 g) is then added to the mixture. The reac... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Boronic acid | Vinyl | c1ccsc1 | c1ccsc1 | c1ccsc1.c1ccccc1 | HBr.B | O1CCOCC1 | null | null | C=C(C)Br.O=Cc1sc(-c2ccc(C(F)(F)F)cc2)cc1B(O)O>O1CCOCC1>C=C(C)c1cc(-c2ccc(C(F)(F)F)cc2)sc1C=O |
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