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-30abbb25505948a5b8ad4e2f8ce04c26 | O=c1[nH]c2c3ccccc3ncc2n1C1CCN(Cc2ccccc2)CC1>>O=c1[nH]c2c3ccccc3ncc2n1C1CCNCC1 | C1(=CC=CC=C1)CN1CCC(CC1)N1C(NC2=C1C=NC=1C=CC=CC21)=O>>N1CCC(CC1)N1C(NC2=C1C=NC=1C=CC=CC21)=O | c1ccc(C[N:18]2[CH2:17][CH2:16][CH:15]([n:14]3[c:2](=[O:1])[nH:3][c:4]4[c:5]5[cH:6][cH:7][cH:8][cH:9][c:10]5[n:11][cH:12][c:13]43)[CH2:20][CH2:19]2)cc1>>[O:1]=[c:2]1[nH:3][c:4]2[c:5]3[cH:6][cH:7][cH:8][cH:9][c:10]3[n:11][cH:12][c:13]2[n:14]1[CH:15]1[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]1 | O=c1[nH]c2c3ccccc3ncc2n1C1CCN(Cc2ccccc2)CC1 | O=c1[nH]c2c3ccccc3ncc2n1C1CCNCC1 | null | [Pd] | null | Deprotection | Hydrogenolysis of tertiary amines | cd3c1aa319cad45f383f17cc0b8bfc8337d7078d779f654933f9a447e64292a5 | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | O=c1[nH]c2c3ccccc3ncc2n1C1CCNCC1 | [C:1]-[C:2]-[N;H0;D3;+0:3](-C-c1:c:c:c:c:c:1)-[C:4]-[C:5]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[C:5] | 98.5 | [{"value": 98.5, "product": "N1CCC(CC1)N1C(NC2=C1C=NC=1C=CC=CC21)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared analogously to Example A3f) from 1,3-dihydro-3-[1-(phenylmethyl)-4-piperidinyl]-2(2H)-imidazo[4,5-c]quinolone by hydrogenolysis in the presence of palladium/charcoal in a yield of 98.5% of theory. Colourless crystals, Rf=0.63 (FM1).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.C1CC[NH]CC1 | C1CCNCC1 | c1ccc2c(c1)ncc1nc[nH]c12.C1CCNCC1 | Other | [Pd] | null | null | O=c1[nH]c2c3ccccc3ncc2n1C1CCN(Cc2ccccc2)CC1>[Pd]>O=c1[nH]c2c3ccccc3ncc2n1C1CCNCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2695880349cf4662a892b70f0c5fdb03 | BrCc1ccccc1.O=Cc1ccc(O)cc1>>O=Cc1ccc(OCc2ccccc2)cc1 | OC1=CC=C(C=O)C=C1.[OH-].[Na+].C(C1=CC=CC=C1)Br>>C1(=CC=CC=C1)COC1=CC=C(C=O)C=C1 | Br[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[cH:15][cH:16]1>>[O:1]=[CH:2][c:3]1[cH:4][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]1 | BrCc1ccccc1.O=Cc1ccc(O)cc1 | O=Cc1ccc(OCc2ccccc2)cc1 | null | null | O.C(C)O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | null | [] | null | null | null | null | To a solution of 36.6 g (0.3 mol) of 4-hydroxybenzaldehyde in 100 ml of ethanol were added dropwise, one after another, a solution of 12.0 g (0.3 mol) of sodium hydroxide in 100 ml of water and a solution of 36.5 ml of (0.307 mol) of benzylbromide in 100 ml of ethanol and the mixture was then kept for 1 hour at 50° C. ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HBr | O.C(C)O | null | null | BrCc1ccccc1.O=Cc1ccc(O)cc1>O.C(C)O>O=Cc1ccc(OCc2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bc115b73d8254c46b155ef5962d23ab0 | Fc1cccnc1.c1ccc(CN2CCNCC2)cc1>>c1ccc(CN2CCNC(c3cccnc3)C2)cc1 | C1(=CC=CC=C1)[Li].FC=1C=NC=CC1.C1(=CC=CC=C1)CN1CCNCC1.C1CCCCC1.C(C)OCC>>C1(=CC=CC=C1)CN1CC(NCC1)C=1C=NC=CC1 | F[c:11]1[cH:12][cH:13][cH:14][n:15][cH:16]1.[cH:1]1[cH:2][cH:3][c:4]([CH2:5][N:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:17]2)[cH:18][cH:19]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][N:6]2[CH2:7][CH2:8][NH:9][CH:10]([c:11]3[cH:12][cH:13][cH:14][n:15][cH:16]3)[CH2:17]2)[cH:18][cH:19]1 | Fc1cccnc1.c1ccc(CN2CCNCC2)cc1 | c1ccc(CN2CCNC(c3cccnc3)C2)cc1 | null | null | C(C)OCC | C-C Coupling | OtherReaction | 23e4a9ad56169b872003f95d1a4758f21f61340ab373ed60277b1e0aee0766aa | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ccc(CN2CCNC(c3cccnc3)C2)cc1 | F-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[C:7]-[#7:8]1-[C:9]-[CH2;D2;+0:10]-[#7:11]-[C:12]-[C:13]-1>>[C:7]-[#7:8]1-[C:9]-[CH;D3;+0:10](-[c;H0;D3;+0:1]2:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:2)-[#7:11]-[C:12]-[C:13]-1 | null | [] | null | null | 2.5 | HOUR | To a solution of 5.0 g (0.0515 mol) of 3-fluoropyridine and 43.5 ml of 1-(phenylmethyl)piperazine in 300 ml of anhydrous diethylether was added dropwise, at boiling temperature, within 2.5 hours, 56 ml (0.112 mol) of a 2 molar solution of phenyl-lithium in a cyclohexane-diethylether mixture (7/3 v/v) and the resulting ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccncc1.C1C[NH]CCN1 | C1C[NH]CCN1.c1ccncc1 | c1ccccc1.C1C[NH]CCN1.c1ccncc1 | HF | C(C)OCC | null | 2.5 | Fc1cccnc1.c1ccc(CN2CCNCC2)cc1>C(C)OCC>c1ccc(CN2CCNC(c3cccnc3)C2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e0a39eff4aed4211888dcddb714a3e82 | CC(C)(C)OC(=O)N1CCNCC1.O=C1CCN(Cc2ccccc2)CC1>>CC(C)(C)OC(=O)N1CCN(C2CCN(Cc3ccccc3)CC2)CC1 | C(#N)[BH3-].[Na+].C(C)(=O)O.CC(C)(OC(=O)N1CCNCC1)C.C1(=CC=CC=C1)CN1CCC(CC1)=O.C(C)(=O)O>>CC(C)(OC(=O)N1CCN(CC1)C1CCN(CC1)CC1=CC=CC=C1)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:25][CH2:26]1.O=[C:12]1[CH2:13][CH2:14][N:15]([CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[CH2:23][CH2:24]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([CH:12]2[CH2:13][CH2:14][N:15]([CH2:16][c:17]3[... | CC(C)(C)OC(=O)N1CCNCC1.O=C1CCN(Cc2ccccc2)CC1 | CC(C)(C)OC(=O)N1CCN(C2CCN(Cc3ccccc3)CC2)CC1 | null | null | CO | Heteroatom Alkylation and Arylation | reductive amination | 3867f2fd8ce8b2c699b684fd69bdf100d4cbae24f7133e200714863bfda8a1fd | 99acf13bfcfe579f51ccb82c65e4ca039ee7ca9b6fcd2747a3d9a292a88e564e | c1ccc(CN2CCC(N3CCNCC3)CC2)cc1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#7:4]1-[C:3]-[C:2]-[CH;D3;+0:1](-[N;H0;D3;+0:10]2-[C:11]-[C:12]-[#7:7]-[C:8]-[C:9]-2)-[C:6]-[C:5]-1 | null | [] | null | null | 18 | HOUR | A solution of 15.0 g ( 0.8054 mol) of 1-(1,1-dimethylethoxycarbonyl)piperazine and 14.26 ml (0.08053 mol) of 1-(phenylmethyl)-4-piperidinone in 250 ml of methanol was adjusted to a pH of between 5 and 6 by dropwise addition of acetic acid and mixed in batches with a total of 4.13 g ( 0.0624 mol) of 95% sodium cyanoboro... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Tertiary amine | C1C[NH]CCN1.C1CC[NH]CC1 | C1C[NH]CC[NH]1.C1CC[NH]CC1 | C1C[NH]CC[NH]1.C1CC[NH]CC1.c1ccccc1 | Other | CO | null | 18 | CC(C)(C)OC(=O)N1CCNCC1.O=C1CCN(Cc2ccccc2)CC1>CO>CC(C)(C)OC(=O)N1CCN(C2CCN(Cc3ccccc3)CC2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6964bfee2a7948d7be33bb4837578412 | CC(C)(C)OC(=O)N1CCN(C2CCN(Cc3ccccc3)CC2)CC1>>CC(C)(C)OC(=O)N1CCN(C2CCNCC2)CC1 | CC(C)(OC(=O)N1CCN(CC1)C1CCN(CC1)CC1=CC=CC=C1)C>>CC(C)(OC(=O)N1CCN(CC1)C1CCNCC1)C | c1ccc(C[N:15]2[CH2:14][CH2:13][CH:12]([N:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:19][CH2:18]3)[CH2:17][CH2:16]2)cc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([CH:12]2[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]2)[CH2:18][CH2:19]1 | CC(C)(C)OC(=O)N1CCN(C2CCN(Cc3ccccc3)CC2)CC1 | CC(C)(C)OC(=O)N1CCN(C2CCNCC2)CC1 | null | [OH-].[OH-].[Pd+2] | null | Deprotection | Hydrogenolysis of tertiary amines | cd3c1aa319cad45f383f17cc0b8bfc8337d7078d779f654933f9a447e64292a5 | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | C1CC(N2CCNCC2)CCN1 | [C:1]-[C:2]-[N;H0;D3;+0:3](-C-c1:c:c:c:c:c:1)-[C:4]-[C:5]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[C:5] | 79.7 | [{"value": 79.7, "product": "CC(C)(OC(=O)N1CCN(CC1)C1CCNCC1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared analogously to Example A3f) from 1-(1,1-dimethyl-ethoxycarbonyl)-4-[1-(phenylmethyl)-4-piperidinyl]piperazine by hydrogenolysis, but using Pearlman's catalyst instead of palladium/charcoal, in a yield of 79.7% of theory.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.C1CC[NH]CC1 | C1CCNCC1 | C1C[NH]CC[NH]1.C1CCNCC1 | Other | [OH-].[OH-].[Pd+2] | null | null | CC(C)(C)OC(=O)N1CCN(C2CCN(Cc3ccccc3)CC2)CC1>[OH-].[OH-].[Pd+2]>CC(C)(C)OC(=O)N1CCN(C2CCNCC2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-be8a991cb10f48eda9f0824b1e001707 | CC(C)(C)OC(=O)N1CCN(C2CCNCC2)CC1.O=C1CCCCC1>>CC(C)(C)OC(=O)N1CCN(C2CCN(C3CCCCC3)CC2)CC1 | CC(C)(OC(=O)N1CCN(CC1)C1CCNCC1)C.C1(CCCCC1)=O>>CC(C)(OC(=O)N1CCN(CC1)C1CCN(CC1)C1CCCCC1)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([CH:12]2[CH2:13][CH2:14][NH:15][CH2:22][CH2:23]2)[CH2:24][CH2:25]1.O=[C:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([CH:12]2[CH2:13][CH2:14][N:15]([CH:16]3[CH2:17][C... | CC(C)(C)OC(=O)N1CCN(C2CCNCC2)CC1.O=C1CCCCC1 | CC(C)(C)OC(=O)N1CCN(C2CCN(C3CCCCC3)CC2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | reductive amination | aeaa50921d4b5ac6d0d449acc673c53dade01d5d58c6e405477a000ef54c9d5c | 99acf13bfcfe579f51ccb82c65e4ca039ee7ca9b6fcd2747a3d9a292a88e564e | C1CCC(N2CCC(N3CCNCC3)CC2)CC1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[CH;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5])-[C:9]-[C:10] | 99 | [{"value": 99.0, "product": "CC(C)(OC(=O)N1CCN(CC1)C1CCN(CC1)C1CCCCC1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared analogously to Example A19a) from 1-(1,1-dimethyl-ethoxycarbonyl)-4-(4-piperidinyl)piperazine and cyclohexanone in a yield of 99% of theory. Colourless, highly viscous oil.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Tertiary amine | C1CCNCC1.C1CCCCC1 | C1CC[NH]CC1.C1CCCCC1 | C1C[NH]CC[NH]1.C1CC[NH]CC1.C1CCCCC1 | Other | null | null | null | CC(C)(C)OC(=O)N1CCN(C2CCNCC2)CC1.O=C1CCCCC1>>CC(C)(C)OC(=O)N1CCN(C2CCN(C3CCCCC3)CC2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f07c05b879ca4bf6b1bcdcb97110346b | CCN1CCC(=O)CC1.c1ccc(CN2CCNCC2)cc1>>CCN1CCC(N2CCN(Cc3ccccc3)CC2)CC1 | C(C)N1CCC(CC1)=O.C1(=CC=CC=C1)CN1CCNCC1>>C(C)N1CCC(CC1)N1CCN(CC1)CC1=CC=CC=C1 | O=[C:6]1[CH2:5][CH2:4][N:3]([CH2:2][CH3:1])[CH2:21][CH2:20]1.[NH:7]1[CH2:8][CH2:9][N:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[CH2:18][CH2:19]1>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][CH:6]([N:7]2[CH2:8][CH2:9][N:10]([CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[CH2:18][CH2:19]2)[CH2:20][CH2:21]1 | CCN1CCC(=O)CC1.c1ccc(CN2CCNCC2)cc1 | CCN1CCC(N2CCN(Cc3ccccc3)CC2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | reductive amination | 2ed33bf1e79823cd6a6e4435985f437473235273b777b8d263fc309ca9eff86a | 99acf13bfcfe579f51ccb82c65e4ca039ee7ca9b6fcd2747a3d9a292a88e564e | c1ccc(CN2CCN(C3CCNCC3)CC2)cc1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#7:7]1-[C:8]-[C:9]-[N;H0;D3;+0:10](-[CH;D3;+0:1]2-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-2)-[C:11]-[C:12]-1 | 71 | [{"value": 71.0, "product": "C(C)N1CCC(CC1)N1CCN(CC1)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared analogously to Example A19a) from 1-ethyl-4-piperidinone and 1-(phenylmethyl)piperazine in a yield of 71% of theory. Colourless, amorphous substance, Rf=0.46 (FM4).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Tertiary amine | C1CC[NH]CC1.C1CNCC[NH]1 | C1CC[NH]CC1.C1C[NH]CC[NH]1 | C1CC[NH]CC1.C1C[NH]CC[NH]1.c1ccccc1 | Other | null | null | null | CCN1CCC(=O)CC1.c1ccc(CN2CCNCC2)cc1>>CCN1CCC(N2CCN(Cc3ccccc3)CC2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7067cbc152254b86b5c05ae99b72eb8b | CC=O.O=C(OCc1ccccc1)N1CCC(C2CCNCC2)CC1>>CCN1CCC(C2CCN(C(=O)OCc3ccccc3)CC2)CC1 | C(#N)[BH3-].[Na+].CC1=C(C(=CC(=C1)C2(C3=CC=CC=C3S(=O)(=O)O2)C4=CC(=C(C(=C4)Br)O)C)Br)O.C1(=CC=CC=C1)COC(=O)N1CCC(CC1)C1CCNCC1.C(C)=O>>C(C)N1CCC(CC1)C1CCN(CC1)C(=O)OCC1=CC=CC=C1 | O=[CH:2][CH3:1].[NH:3]1[CH2:4][CH2:5][CH:6]([CH:7]2[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[CH2:21][CH2:22]2)[CH2:23][CH2:24]1>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][CH:6]([CH:7]2[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:2... | CC=O.O=C(OCc1ccccc1)N1CCC(C2CCNCC2)CC1 | CCN1CCC(C2CCN(C(=O)OCc3ccccc3)CC2)CC1 | null | null | Cl.CO.CO.O | Heteroatom Alkylation and Arylation | reductive amination | d0e659bc8d1e29e09a61320b4c537e66ad57335a51368c8bd48de9bdffa59372 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=C(OCc1ccccc1)N1CCC(C2CCNCC2)CC1 | O=[CH;D2;+0:1]-[C;D1;H3:2].[C:3]-[C:4]-[NH;D2;+0:5]-[C:6]-[C:7]>>[C:3]-[C:4]-[N;H0;D3;+0:5](-[CH2;D2;+0:1]-[C;D1;H3:2])-[C:6]-[C:7] | null | [] | null | null | null | null | To a solution of 18.14 g (0.061 mol) of 1-(phenylmethoxycarbonyl)-4-(4-piperidinyl)piperidine in 450 ml of a methanol/water mixture (1/1 v/v) were added, with stirring, whilst maintaining a temperature of 15 to 20° C., 10.05 g (0.152 mol) of 95% sodium cyanoborohydride and 50 mg of bromocresol purple. Then a solution o... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.C1CC[NH]CC1.c1ccccc1 | Other | Cl.CO.CO.O | null | null | CC=O.O=C(OCc1ccccc1)N1CCC(C2CCNCC2)CC1>Cl.CO.CO.O>CCN1CCC(C2CCN(C(=O)OCc3ccccc3)CC2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5a75cfbb2ebe4d1da82d9af7f8daad6f | CCN1CCC(C2CCN(C(=O)OCc3ccccc3)CC2)CC1>>CCN1CCC(C2CCNCC2)CC1 | [H][H].C(C)N1CCC(CC1)C1CCN(CC1)C(=O)OCC1=CC=CC=C1.O.C(C)(=O)O.[H][H]>>C(C)N1CCC(CC1)C1CCNCC1 | O=C(OCc1ccccc1)[N:10]1[CH2:9][CH2:8][CH:7]([CH:6]2[CH2:5][CH2:4][N:3]([CH2:2][CH3:1])[CH2:14][CH2:13]2)[CH2:12][CH2:11]1>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][CH:6]([CH:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]2)[CH2:13][CH2:14]1 | CCN1CCC(C2CCN(C(=O)OCc3ccccc3)CC2)CC1 | CCN1CCC(C2CCNCC2)CC1 | null | [Pd] | CO | Reduction | Hydrogenolysis of tertiary amines | ce0208fabe82d1244d7db7b6f7627b1b39a8cf3492e02720426849e93718e81c | 20c36f41eeb07c3ba4437b51ba72e8ff3c22d0b27e7197b0e9af3127f331149f | C1CC(C2CCNCC2)CCN1 | O=C(-O-C-c1:c:c:c:c:c:1)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | null | [] | null | null | null | null | A solution of 7.6 g (0.023 mol) of 1-ethyl-4-[1-(phenylmethoxy-carbonyl)-4-piperidinyl]piperidine in a mixture of 70 ml of methanol, 30 ml of water and 10 ml of glacial acetic acid was hydrogenated in the presence of 10% palladium/charcoal at room temperature and 3 bar of hydrogen pressure until the uptake of hydrogen ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Secondary amine | c1ccccc1.C1CC[NH]CC1 | C1CCNCC1 | C1CC[NH]CC1.C1CCNCC1 | HO- | [Pd].CO | null | null | CCN1CCC(C2CCN(C(=O)OCc3ccccc3)CC2)CC1>[Pd].CO>CCN1CCC(C2CCNCC2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-94fcb51b47c845f0ae6891a69974f9e6 | CN1CCCN(C2CCN(Cc3ccccc3)CC2)CC1>>CN1CCCN(C2CCNCC2)CC1 | CN1CCN(CCC1)C1CCN(CC1)CC1=CC=CC=C1>>CN1CCN(CCC1)C1CCNCC1 | c1ccc(C[N:10]2[CH2:9][CH2:8][CH:7]([N:6]3[CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[CH2:14][CH2:13]3)[CH2:12][CH2:11]2)cc1>>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][N:6]([CH:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]2)[CH2:13][CH2:14]1 | CN1CCCN(C2CCN(Cc3ccccc3)CC2)CC1 | CN1CCCN(C2CCNCC2)CC1 | null | [OH-].[OH-].[Pd+2] | null | Deprotection | Hydrogenolysis of tertiary amines | cd3c1aa319cad45f383f17cc0b8bfc8337d7078d779f654933f9a447e64292a5 | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | C1CNCCN(C2CCNCC2)C1 | [C:1]-[C:2]-[N;H0;D3;+0:3](-C-c1:c:c:c:c:c:1)-[C:4]-[C:5]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[C:5] | null | [] | null | null | null | null | Prepared analogously to Example A3f) from hexahydro-1-methyl-4-[1-(phenylmethyl)-4-piperidinyl]-1H-1,4-diazepine by hydrogenolysis, but using Pearlman's catalyst instead of palladium/charcoal, in a quantitative yield. Colourless viscous oil.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.C1CC[NH]CC1 | C1CCNCC1 | C1C[NH]CC[NH]C1.C1CCNCC1 | Other | [OH-].[OH-].[Pd+2] | null | null | CN1CCCN(C2CCN(Cc3ccccc3)CC2)CC1>[OH-].[OH-].[Pd+2]>CN1CCCN(C2CCNCC2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c18f012680a7404e9201c62d1b1b5f4d | CC(C)(C)OC(=O)N1CCC(C(=O)O)CC1.CN1CCNCC1>>CN1CCN(C(=O)C2CCN(C(=O)OC(C)(C)C)CC2)CC1 | N.CC(C)(OC(=O)N1CCC(CC1)C(=O)O)C.CN1CCNCC1.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.[B-](F)(F)(F)F>>CC(C)(OC(=O)N1CCC(CC1)C(=O)N1CCN(CC1)C)C | O[C:6](=[O:7])[CH:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]1.[CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:21][CH2:22]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[CH:8]2[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]2)[C... | CC(C)(C)OC(=O)N1CCC(C(=O)O)CC1.CN1CCNCC1 | CN1CCN(C(=O)C2CCN(C(=O)OC(C)(C)C)CC2)CC1 | null | null | ClCCl.CO | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | be4b86020a065d99e289e528d425e25dd0737bea0f2fd81bb05a4d03f92a7d75 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(C1CCNCC1)N1CCNCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1)-[C:5] | 76 | [{"value": 76.0, "product": "CC(C)(OC(=O)N1CCC(CC1)C(=O)N1CCN(CC1)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared analogously to Example A15a) from 1-(1,1-dimethylethoxycarbonyl)-4-piperidinecarboxylic acid and 1-methylpiperazine in the presence of TBTU in a yield of 76% of theory. Colourless, amorphous substance, Rf=0.64 (eluant: dichloromethane/methanol/conc. ammonia 50/50/1 v/v/v).
Conditions: See reaction.notes.proced... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.C1CC[NH]CC1 | HO- | ClCCl.CO | null | null | CC(C)(C)OC(=O)N1CCC(C(=O)O)CC1.CN1CCNCC1>ClCCl.CO>CN1CCN(C(=O)C2CCN(C(=O)OC(C)(C)C)CC2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5eacc857d6964c20a82176fc7227bf45 | CC(C)(C)OC(=O)N[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)O.c1cc(N2CCNCC2)ccn1>>CC(C)(C)OC(=O)N[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)N1CCN(c2ccncc2)CC1 | N([C@@H](CCCCNC(=O)OCC1=CC=CC=C1)C(=O)O)C(=O)OC(C)(C)C.CCN(C(C)C)C(C)C.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.[B-](F)(F)(F)F.C=1C=CC2=C(C1)N=NN2O.N1=CC=C(C=C1)N1CCNCC1>>CC(C)(OC(=O)N[C@@H](CCCCNC(=O)OCC1=CC=CC=C1)C(=O)N1CCN(CC1)C1=CC=NC=C1)C | O[C:25]([C@@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:16])[O:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)=[O:26].[NH:27]1[CH2:28][CH2:29][N:30]([c:31]2[cH:32][cH:33][n:34][cH:35][cH:36]2)[CH2:37][CH2:38]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5]... | CC(C)(C)OC(=O)N[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)O.c1cc(N2CCNCC2)ccn1 | CC(C)(C)OC(=O)N[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)N1CCN(c2ccncc2)CC1 | null | null | CN(C)C=O.CN(C=O)C | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ed26ef5eea92a0cc433b3f89a34f4c61724425fa15a9d0ec83a0f7a903eec831 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(NCCCCCC(=O)N1CCN(c2ccncc2)CC1)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12].[#7:13]1-[C:14]-[C:15]-[NH;D2;+0:16]-[C:17]-[C:18]-1>>[C:4]-[C:3](-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:... | null | [] | null | null | null | null | To a mixture of 18.8 g (0.0494 mol) of Boc-Lys(Z)-OH, 6.5 g (0.05 mol) of DIEA, 16 g (0.05 mol) of TBTU, 6.6 g (0.049 mol) of HOBt and 100 ml of dimethylformamide were added dropwise, with stirring, 8.1 g (0.0494 mol) of 1-(4-pyridinyl)piperazine, dissolved in 40 ml of DMF, and the mixture was stirred over-night at roo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | HO- | CN(C)C=O.CN(C=O)C | null | null | CC(C)(C)OC(=O)N[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)O.c1cc(N2CCNCC2)ccn1>CN(C)C=O.CN(C=O)C>CC(C)(C)OC(=O)N[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)N1CCN(c2ccncc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-000db519bd8e41afb6aaf1c6eb285b2e | CC(C)(C)OC(=O)NCCCC[C@H](NC(=O)OCc1ccccc1)C(=O)O.c1cc(N2CCNCC2)ccn1>>CC(C)(C)OC(=O)NCCCC[C@H](NC(=O)OCc1ccccc1)C(=O)N1CCN(c2ccncc2)CC1 | N([C@@H](CCCCNC(=O)OC(C)(C)C)C(=O)O)C(=O)OCC1=CC=CC=C1.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.[B-](F)(F)(F)F.C=1C=CC2=C(C1)N=NN2O.N1=CC=C(C=C1)N1CCNCC1.CCN(C(C)C)C(C)C>>C1(=CC=CC=C1)COC(=O)N[C@@H](CCCCNC(=O)OC(C)(C)C)C(=O)N1CCN(CC1)C1=CC=NC=C1 | O[C:25]([C@H:13]([CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[NH:14][C:15](=[O:16])[O:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)=[O:26].[NH:27]1[CH2:28][CH2:29][N:30]([c:31]2[cH:32][cH:33][n:34][cH:35][cH:36]2)[CH2:37][CH2:38]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][... | CC(C)(C)OC(=O)NCCCC[C@H](NC(=O)OCc1ccccc1)C(=O)O.c1cc(N2CCNCC2)ccn1 | CC(C)(C)OC(=O)NCCCC[C@H](NC(=O)OCc1ccccc1)C(=O)N1CCN(c2ccncc2)CC1 | null | null | CN(C=O)C | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ed26ef5eea92a0cc433b3f89a34f4c61724425fa15a9d0ec83a0f7a903eec831 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(NCC(=O)N1CCN(c2ccncc2)CC1)OCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[C:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1 | null | [] | null | null | null | null | To a mixture of 100 g (0.263 mol) of Z-Lys(Boc)-OH, 86.1 g (0.268 mol) of TBTU and 36.3 g (0.263 mol) of HOBt in 600 ml of dimethylformamide were added 43.0 g (0.263 mol) of 1-(4-pyridinyl)-piperazine and 47.2 ml (0.268 mol) of DIEA with stirring and the mixture was stirred overnight at room temperature. The reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | HO- | CN(C=O)C | null | null | CC(C)(C)OC(=O)NCCCC[C@H](NC(=O)OCc1ccccc1)C(=O)O.c1cc(N2CCNCC2)ccn1>CN(C=O)C>CC(C)(C)OC(=O)NCCCC[C@H](NC(=O)OCc1ccccc1)C(=O)N1CCN(c2ccncc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-35013854a72d4f6ca5d1eef231b945b6 | CC(C)(C)OC(=O)N[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)N1CCN(c2ccncc2)CC1>>N[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)N1CCN(c2ccncc2)CC1 | CC(C)(OC(=O)N[C@@H](CCCCNC(=O)OCC1=CC=CC=C1)C(=O)N1CCN(CC1)C1=CC=NC=C1)C.FC(C(=O)O)(F)F.C(O)([O-])=O.[Na+]>>C1(=CC=CC=C1)COC(=O)NCCCC[C@H](N)C(=O)N1CCN(CC1)C1=CC=NC=C1 | CC(C)(C)OC(=O)[NH:1][C@@H:2]([CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:9])[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[C:18](=[O:19])[N:20]1[CH2:21][CH2:22][N:23]([c:24]2[cH:25][cH:26][n:27][cH:28][cH:29]2)[CH2:30][CH2:31]1>>[NH2:1][C@@H:2]([CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:9])[O:10][CH2:11][c... | CC(C)(C)OC(=O)N[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)N1CCN(c2ccncc2)CC1 | N[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)N1CCN(c2ccncc2)CC1 | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C(NCCCCCC(=O)N1CCN(c2ccncc2)CC1)OCc1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#7:6](-[C:7])-[C:8]>>[C:7]-[#7:6](-[C:4](=[O;D1;H0:5])-[C:2](-[C:3])-[NH2;D1;+0:1])-[C:8] | null | [] | null | null | 8 | HOUR | To a mixture of 24.2 g (46 mmol) of 1-[N2-(1,1-dimethylethoxycarbonyl)-N6-(phenylmethoxycarbonyl)-L-lysyl]-4-(4-pyridinyl)piperazine and 150 ml of methylene chloride were added 50 ml of trifluoroacetic acid and the reaction mixture was stirred overnight at room temperature. The reaction mixture was neutralised by the a... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | HO- | C(Cl)Cl | null | 8 | CC(C)(C)OC(=O)N[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)N1CCN(c2ccncc2)CC1>C(Cl)Cl>N[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)N1CCN(c2ccncc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b3c063f2fb514a9ebd1c8ae19f5bd66a | CC(C)(C)OC(=O)NC(Cc1ccncc1)C(=O)N1CCN(c2ccncc2)CC1>>NC(Cc1ccncc1)C(=O)N1CCN(c2ccncc2)CC1 | CC(C)(OC(=O)NC(CC1=CC=NC=C1)C(=O)N1CCN(CC1)C1=CC=NC=C1)C.Cl>>Cl.N1=CC=C(C=C1)N1CCN(CC1)C(C(N)CC1=CC=NC=C1)=O | CC(C)(C)OC(=O)[NH:2][CH:3]([CH2:4][c:5]1[cH:6][cH:7][n:8][cH:9][cH:10]1)[C:11](=[O:12])[N:13]1[CH2:14][CH2:15][N:16]([c:17]2[cH:18][cH:19][n:20][cH:21][cH:22]2)[CH2:23][CH2:24]1>>[NH2:2][CH:3]([CH2:4][c:5]1[cH:6][cH:7][n:8][cH:9][cH:10]1)[C:11](=[O:12])[N:13]1[CH2:14][CH2:15][N:16]([c:17]2[cH:18][cH:19][n:20][cH:21][cH... | CC(C)(C)OC(=O)NC(Cc1ccncc1)C(=O)N1CCN(c2ccncc2)CC1 | NC(Cc1ccncc1)C(=O)N1CCN(c2ccncc2)CC1 | null | null | CO | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C(CCc1ccncc1)N1CCN(c2ccncc2)CC1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#7:6](-[C:7])-[C:8]>>[C:7]-[#7:6](-[C:4](=[O;D1;H0:5])-[C:2](-[C:3])-[NH2;D1;+0:1])-[C:8] | null | [] | 40 | CELSIUS | null | null | 16.4 g (0.04 mol) of 1-[N-[(1,1-dimethylethoxy)carbonyl]-3-(4-pyridinyl)-D,L-alanyl]-4-(4-pyridinyl)-piperazine, dissolved in 100 ml of methanol, were mixed with 20 ml of ethereal hydrochloric acid and the reaction mixture was heated to 40° C. The desired compound crystallised out of the reaction mixture.
Conditions: S... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccncc1.C1C[NH]CC[NH]1.c1ccncc1 | HO- | CO | 40 | null | CC(C)(C)OC(=O)NC(Cc1ccncc1)C(=O)N1CCN(c2ccncc2)CC1>CO>NC(Cc1ccncc1)C(=O)N1CCN(c2ccncc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-19efd7b90aef4a038c0b9964b6ddaf4d | COC(=O)[C@@H](N)CCCCNC(=O)OC(C)(C)C.COc1cccc(CCNC(=O)N[C@H](Cc2cc(Br)c(O)c(Br)c2)C(=O)O)c1>>COc1cccc(CCNC(=O)N[C@H](Cc2cc(Br)c(O)c(Br)c2)C(=O)N(C)[C@@H](CCCCNC(=O)OC(C)(C)C)C(=O)O)c1 | BrC=1C=C(C[C@@H](NC(=O)NCCC2=CC(=CC=C2)OC)C(=O)O)C=C(C1O)Br.CCN(C(C)C)C(C)C.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.[B-](F)(F)(F)F.C=1C=CC2=C(C1)N=NN2O.N[C@@H](CCCCNC(=O)OC(C)(C)C)C(=O)OC>>CN([C@@H](CCCCNC(=O)OC(C)(C)C)C(=O)O)C([C@H](NC(=O)NCCC1=CC(=CC=C1)OC)CC1=CC(=C(C(=C1)Br)O)Br)=O | [NH2:27][C@@H:29]([CH2:30][CH2:31][CH2:32][CH2:33][NH:34][C:35](=[O:36])[O:37][C:38]([CH3:39])([CH3:40])[CH3:41])[C:42](=[O:43])[O:44][CH3:28].O[C:25]([C@H:14]([NH:13][C:11]([NH:10][CH2:9][CH2:8][c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:45]1)=[O:12])[CH2:15][c:16]1[cH:17][c:18]([Br:19])[c:20]([OH:21])[c:22]([Br:23... | COC(=O)[C@@H](N)CCCCNC(=O)OC(C)(C)C.COc1cccc(CCNC(=O)N[C@H](Cc2cc(Br)c(O)c(Br)c2)C(=O)O)c1 | COc1cccc(CCNC(=O)N[C@H](Cc2cc(Br)c(O)c(Br)c2)C(=O)N(C)[C@@H](CCCCNC(=O)OC(C)(C)C)C(=O)O)c1 | null | null | CN(C=O)C | Acylation | OtherReaction | c1b73484cf9c1bfcd252d508ce2e786d4eb62782f08ee517550484708afee857 | b6ea84a48ff66c67f13726a349ffe1c0217e9604a17d926d0500ebd23db847ed | O=C(NCCc1ccccc1)NCCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6]=[O;D1;H0:7].[C:8]-[C:9](-[NH2;D1;+0:10])-[C:11](=[O;D1;H0:12])-[O;H0;D2;+0:13]-[CH3;D1;+0:14]>>[C:4]-[C:3](-[#7:5]-[C:6]=[O;D1;H0:7])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:10](-[CH3;D1;+0:14])-[C:9](-[C:8])-[C:11](=[O;D1;H0:12])-[OH;D1;+0:13] | null | [] | null | null | null | null | To a mixture of 10 g (19.4 mmol) of 3,5-dibromo-N-[[[2-(3-methoxyphenyl)ethyl]amino]carbonyl]-D-tyrosine, 2.6 g (20 mmol) of DIEA, 6.4 g (20 mmol) of TBTU, 2.64 g (19.5 mmol) of HOBt and 200 ml of dimethylformamide was added dropwise, with stirring, a solution of 5.04 g (19.4 mmol) of H-Lys(Boc)-OMe in 50 ml of dimethy... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester.Primary amine | Carboxylic acid.Tertiary amide | null | null | c1ccccc1.c1ccccc1 | HO- | CN(C=O)C | null | null | COC(=O)[C@@H](N)CCCCNC(=O)OC(C)(C)C.COc1cccc(CCNC(=O)N[C@H](Cc2cc(Br)c(O)c(Br)c2)C(=O)O)c1>CN(C=O)C>COc1cccc(CCNC(=O)N[C@H](Cc2cc(Br)c(O)c(Br)c2)C(=O)N(C)[C@@H](CCCCNC(=O)OC(C)(C)C)C(=O)O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-70374705afdb455697fa2afcb8e444c1 | CC(C)(C)OC(=O)NCCCC[C@H](NC(=O)[C@@H](Cc1cc(Cl)c(O)c(Cl)c1)NC(=O)OCc1ccccc1)C(=O)N1CCN(c2ccncc2)CC1>>CC(C)(C)OC(=O)NCCCC[C@H](NC(=O)[C@H](N)Cc1cc(Cl)c(O)c(Cl)c1)C(=O)N1CCN(c2ccncc2)CC1 | [H][H].C1(=CC=CC=C1)COC(=O)N[C@H](CC1=CC(=C(C(=C1)Cl)O)Cl)C(=O)N[C@@H](CCCCNC(=O)OC(C)(C)C)C(=O)N1CCN(CC1)C1=CC=NC=C1.S(=O)(=O)(O)[O-].[K+]>>ClC=1C=C(C[C@@H](N)C(=O)N[C@@H](CCCCNC(=O)OC(C)(C)C)C(=O)N2CCN(CC2)C2=CC=NC=C2)C=C(C1O)Cl | O=C(OCc1ccccc1)[NH:18][C@@H:17]([C:15]([NH:14][C@@H:13]([CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C:29](=[O:30])[N:31]1[CH2:32][CH2:33][N:34]([c:35]2[cH:36][cH:37][n:38][cH:39][cH:40]2)[CH2:41][CH2:42]1)=[O:16])[CH2:19][c:20]1[cH:21][c:22]([Cl:23])[c:24]([OH:25])[c:26]([Cl:2... | CC(C)(C)OC(=O)NCCCC[C@H](NC(=O)[C@@H](Cc1cc(Cl)c(O)c(Cl)c1)NC(=O)OCc1ccccc1)C(=O)N1CCN(c2ccncc2)CC1 | CC(C)(C)OC(=O)NCCCC[C@H](NC(=O)[C@H](N)Cc1cc(Cl)c(O)c(Cl)c1)C(=O)N1CCN(c2ccncc2)CC1 | null | [Pd] | CO | Reduction | Hydrogenolysis of amides/imides/carbamates | 087b6600ba91d3df931fe6979f2445c192cbfd59e04fd2d8a10f7c7573ac669f | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | O=C(CCc1ccccc1)NCC(=O)N1CCN(c2ccncc2)CC1 | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7]-[C:8](-[#7:9])=[O;D1;H0:10]>>[#7:9]-[C:8](=[O;D1;H0:10])-[C:7]-[#7:6]-[C:4](=[O;D1;H0:5])-[C:2](-[C:3])-[NH2;D1;+0:1] | null | [] | null | null | null | null | A solution of 6 g (7.9 mmol) of 1-[N2—[N-[(phenylmethoxy)carbonyl]-3,5-dichloro-D-tyrosyl]-N6-[(1,1-dimethylethoxy)carbonyl]-L-lysyl]-4-(4-pyridinyl)-piperazine in a mixture of 200 ml of methanol and 20 ml of aqueous 1 M potassium hydrogen sulphate solution was hydrogenated in the presence of 0.5 g palladium black as c... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccccc1 | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | HO- | [Pd].CO | null | null | CC(C)(C)OC(=O)NCCCC[C@H](NC(=O)[C@@H](Cc1cc(Cl)c(O)c(Cl)c1)NC(=O)OCc1ccccc1)C(=O)N1CCN(c2ccncc2)CC1>[Pd].CO>CC(C)(C)OC(=O)NCCCC[C@H](NC(=O)[C@H](N)Cc1cc(Cl)c(O)c(Cl)c1)C(=O)N1CCN(c2ccncc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a38ba5a0c5bf44e69386ef31e7bf4076 | CC(C)(C)OC(=O)NCCCC[C@H](NC(=O)OCc1ccccc1)C(=O)N1CCN(c2ccncc2)CC1>>CN(C)CCCC[C@H](NC(=O)OCc1ccccc1)C(=O)N1CCN(c2ccncc2)CC1 | CC(C)(OC(=O)NCCCC[C@H](NC(=O)OCC1=CC=CC=C1)C(=O)N1CCN(CC1)C1=CC=NC=C1)C.FC(C(=O)O)(F)F>>CN(CCCC[C@H](NC(=O)OCC1=CC=CC=C1)C(=O)N1CCN(CC1)C1=CC=NC=C1)C | CC(C)(O[C:1](=O)[NH:2][CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]([NH:9][C:10](=[O:11])[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[C:20](=[O:21])[N:22]1[CH2:23][CH2:24][N:25]([c:26]2[cH:27][cH:28][n:29][cH:30][cH:31]2)[CH2:32][CH2:33]1)[CH3:3]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]([NH:9][C:10... | CC(C)(C)OC(=O)NCCCC[C@H](NC(=O)OCc1ccccc1)C(=O)N1CCN(c2ccncc2)CC1 | CN(C)CCCC[C@H](NC(=O)OCc1ccccc1)C(=O)N1CCN(c2ccncc2)CC1 | null | null | ClCCl | Miscellaneous | OtherReaction | 9668db0e82bccb720fd6c09fae93b3629353d141a9ec8cda9eb1024fa28e1bb9 | e47004493024d0530f2b800fc4243eb94d7814aa230ccf48fea0cdbdb3159a24 | O=C(NCC(=O)N1CCN(c2ccncc2)CC1)OCc1ccccc1 | C-C(-C)(-[CH3;D1;+0:1])-O-[C;H0;D3;+0:2](=O)-[NH;D2;+0:3]-[C:4]-[C:5]>>[C:5]-[C:4]-[N;H0;D3;+0:3](-[CH3;D1;+0:2])-[CH3;D1;+0:1] | 97 | [{"value": 97.0, "product": "CN(CCCC[C@H](NC(=O)OCC1=CC=CC=C1)C(=O)N1CCN(CC1)C1=CC=NC=C1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 9.6 g (18.3 mmol) of 1-[N6-[(1,1-dimethylethoxy)carbonyl]-N2-[(phenylmethoxy)carbonyl]-L-lysyl]-4-(4-pyridinyl)-piperazine were stirred overnight in 200 ml of a 5% solution of trifluoroacetic acid in dichloromethane. The reaction mixture was then evaporated down in vacuo. 13.47 g (97% of theory) of the desired 1-[N2-[(... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Tertiary amine | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | HO- | ClCCl | null | null | CC(C)(C)OC(=O)NCCCC[C@H](NC(=O)OCc1ccccc1)C(=O)N1CCN(c2ccncc2)CC1>ClCCl>CN(C)CCCC[C@H](NC(=O)OCc1ccccc1)C(=O)N1CCN(c2ccncc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4a7e541d464a41509c2c63f3d0e4e9e2 | N[C@H](Cc1cc(Br)c(O)c(Br)c1)C(=O)N1CCC(N2CCCCC2)CC1>>N[C@H](Cc1cc(Br)c(O)c(Br)c1)CN1CCC(N2CCCCC2)CC1 | BrC=1C=C(C[C@@H](N)C(=O)N2CCC(CC2)N2CCCCC2)C=C(C1O)Br.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.Cl>>N[C@@H](CN1CCC(CC1)N1CCCCC1)CC1=CC(=C(C(=C1)Br)O)Br | O=[C:13]([C@H:2]([NH2:1])[CH2:3][c:4]1[cH:5][c:6]([Br:7])[c:8]([OH:9])[c:10]([Br:11])[cH:12]1)[N:14]1[CH2:15][CH2:16][CH:17]([N:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)[CH2:24][CH2:25]1>>[NH2:1][C@H:2]([CH2:3][c:4]1[cH:5][c:6]([Br:7])[c:8]([OH:9])[c:10]([Br:11])[cH:12]1)[CH2:13][N:14]1[CH2:15][CH2:16][CH:17]([N:1... | N[C@H](Cc1cc(Br)c(O)c(Br)c1)C(=O)N1CCC(N2CCCCC2)CC1 | N[C@H](Cc1cc(Br)c(O)c(Br)c1)CN1CCC(N2CCCCC2)CC1 | null | null | CO.C1CCOC1 | Reduction | Reduction of tertiary amides to amines | f74c5a050b269ec4da3871c266f01344b7447381f47cda744f8b1e9c225ae62d | c8f3c617792f7a4fae96b8a97dc0ce23461ab85d8a738fe6caacff776ef51ffa | c1ccc(CCCN2CCC(N3CCCCC3)CC2)cc1 | O=[C;H0;D3;+0:1](-[#7:2](-[C:3])-[C:4])-[C:5](-[C:6])-[N;D1;H2:7]>>[C:3]-[#7:2](-[CH2;D2;+0:1]-[C:5](-[C:6])-[N;D1;H2:7])-[C:4] | null | [] | null | null | 30 | MINUTE | To a suspension of 3.8 g (100 mmol) of lithium aluminium hydride in 400 ml of THF were added in batches, with stirring and at room temperature, 14.4 g (20 mmol) of 1-(3,5-dibromo-D-tyrosyl)-4-(1-piperidinyl)-piperidine within 30 minutes. The reaction mixture was kept for 30 minutes at room temperature and refluxed for ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | null | null | null | c1ccccc1.C1CC[NH]CC1.C1CC[NH]CC1 | Other | CO.C1CCOC1 | null | 0.5 | N[C@H](Cc1cc(Br)c(O)c(Br)c1)C(=O)N1CCC(N2CCCCC2)CC1>CO.C1CCOC1>N[C@H](Cc1cc(Br)c(O)c(Br)c1)CN1CCC(N2CCCCC2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5bf4cd61999549b1b00eff1a1f4e86b8 | CC(C)(C)OC(=O)N[C@H](Cc1cc(Br)c(N)c(Br)c1)C(=O)N1CCC(N2CCCCC2)CC1>>CC(C)(C)OC(=O)N[C@H](Cc1cc(Br)c(N)c(Br)c1)CN1CCC(N2CCCCC2)CC1 | C(C)(=O)O.NC1=C(C=C(C[C@@H](NC(=O)OC(C)(C)C)C(=O)N2CCC(CC2)N2CCCCC2)C=C1Br)Br.[BH4-].[Na+]>>NC1=C(C=C(C=C1Br)C[C@H](CN1CCC(CC1)N1CCCCC1)NC(=O)OC(C)(C)C)Br | O=[C:20]([C@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:10][c:11]1[cH:12][c:13]([Br:14])[c:15]([NH2:16])[c:17]([Br:18])[cH:19]1)[N:21]1[CH2:22][CH2:23][CH:24]([N:25]2[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]2)[CH2:31][CH2:32]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]([CH2:10][c... | CC(C)(C)OC(=O)N[C@H](Cc1cc(Br)c(N)c(Br)c1)C(=O)N1CCC(N2CCCCC2)CC1 | CC(C)(C)OC(=O)N[C@H](Cc1cc(Br)c(N)c(Br)c1)CN1CCC(N2CCCCC2)CC1 | null | null | O1CCOCC1 | Reduction | Reduction of tertiary amides to amines | f74c5a050b269ec4da3871c266f01344b7447381f47cda744f8b1e9c225ae62d | c8f3c617792f7a4fae96b8a97dc0ce23461ab85d8a738fe6caacff776ef51ffa | c1ccc(CCCN2CCC(N3CCCCC3)CC2)cc1 | O=[C;H0;D3;+0:1](-[#7:2](-[C:3])-[C:4])-[C:5](-[C:6])-[#7:7]-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[C;D1;H3:14]>>[C:6]-[C:5](-[#7:7]-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[C;D1;H3:14])-[CH2;D2;+0:1]-[#7:2](-[C:3])-[C:4] | null | [] | 5 | CELSIUS | null | null | To a solution of 10 g (0.017 mol) of 1-[4-amino-3,5-dibromo-N-[(1,1-dimethylethoxy)carbonyl]-D-phenylalanyl]-4-(1-piperidinyl)-piperidine in 350 ml of dioxane were added 3.1 g (0.082 mol) of sodium borohydride and the reaction mixture was cooled to 5° C. Then a solution of 4.92 g (0.082 mol) of acetic acid in 100 ml of... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | null | null | null | c1ccccc1.C1CC[NH]CC1.C1CC[NH]CC1 | Other | O1CCOCC1 | 5 | null | CC(C)(C)OC(=O)N[C@H](Cc1cc(Br)c(N)c(Br)c1)C(=O)N1CCC(N2CCCCC2)CC1>O1CCOCC1>CC(C)(C)OC(=O)N[C@H](Cc1cc(Br)c(N)c(Br)c1)CN1CCC(N2CCCCC2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2d6422f61e6349b2ba5da6967bd16711 | CC(C)(C)OC(=O)N[C@H](Cc1cc(Br)c(N)c(Br)c1)CN1CCC(N2CCCCC2)CC1>>Nc1c(Br)cc(C[C@@H](N)CN2CCC(N3CCCCC3)CC2)cc1Br | NC1=C(C=C(C=C1Br)C[C@H](CN1CCC(CC1)N1CCCCC1)NC(=O)OC(C)(C)C)Br.FC(C(=O)O)(F)F>>N[C@@H](CN1CCC(CC1)N1CCCCC1)CC1=CC(=C(C(=C1)Br)N)Br | CC(C)(C)OC(=O)[NH:9][C@H:8]([CH2:7][c:6]1[cH:5][c:3]([Br:4])[c:2]([NH2:1])[c:24]([Br:25])[cH:23]1)[CH2:10][N:11]1[CH2:12][CH2:13][CH:14]([N:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)[CH2:21][CH2:22]1>>[NH2:1][c:2]1[c:3]([Br:4])[cH:5][c:6]([CH2:7][C@@H:8]([NH2:9])[CH2:10][N:11]2[CH2:12][CH2:13][CH:14]([N:15]3[CH2:16... | CC(C)(C)OC(=O)N[C@H](Cc1cc(Br)c(N)c(Br)c1)CN1CCC(N2CCCCC2)CC1 | Nc1c(Br)cc(C[C@@H](N)CN2CCC(N3CCCCC3)CC2)cc1Br | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc(CCCN2CCC(N3CCCCC3)CC2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[C:4])-[NH2;D1;+0:1] | null | [] | 10 | CELSIUS | null | null | To a mixture of 4 g (7 mmol) of (R)-1-[3-(4-amino-3,5-dibromophenyl)-2-[N-[(1,1-dimethylethoxy)carbonyl]-amino]propyl]-4-(1-piperidinyl)-piperidine and 100 ml of methylene chloride, 40 ml of trifluoroacetic acid were slowly added dropwise, with stirring, at 10° C. The reaction mixture was stirred for 2 hours at room te... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.C1CC[NH]CC1.C1CC[NH]CC1 | HO- | C(Cl)Cl | 10 | null | CC(C)(C)OC(=O)N[C@H](Cc1cc(Br)c(N)c(Br)c1)CN1CCC(N2CCCCC2)CC1>C(Cl)Cl>Nc1c(Br)cc(C[C@@H](N)CN2CCC(N3CCCCC3)CC2)cc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b6da2c7d633344979b2212fdf8c904e9 | CO.COc1c(Br)cc(C[C@@H](N)C(=O)O)cc1Br>>CN[C@H](Cc1cc(Br)c(OC)c(Br)c1)C(=O)O | N.Cl.BrC=1C=C(C[C@@H](N)C(=O)O)C=C(C1OC)Br.CO.Cl>>CN[C@H](CC1=CC(=C(C(=C1)Br)OC)Br)C(=O)O | O[CH3:1].[NH2:2][C@H:3]([CH2:4][c:5]1[cH:6][c:7]([Br:8])[c:9]([O:10][CH3:11])[c:12]([Br:13])[cH:14]1)[C:15](=[O:16])[OH:17]>>[CH3:1][NH:2][C@H:3]([CH2:4][c:5]1[cH:6][c:7]([Br:8])[c:9]([O:10][CH3:11])[c:12]([Br:13])[cH:14]1)[C:15](=[O:16])[OH:17] | CO.COc1c(Br)cc(C[C@@H](N)C(=O)O)cc1Br | CN[C@H](Cc1cc(Br)c(OC)c(Br)c1)C(=O)O | null | null | ClCCl.C(C)(=O)OCC.C1CCCCC1.CO | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | 2412ad2bf55d1b100ccf5afbea6bdcdff3d6343a60ada495e0ca3cd28bcff6ae | ad33f63a1954b48a4aeedeefe37c79b586f0b8ced78f080e8788da76a64e1b19 | c1ccccc1 | O-[CH3;D1;+0:1].[C:2]-[C:3](-[NH2;D1;+0:4])-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]>>[C:2]-[C:3](-[NH;D2;+0:4]-[CH3;D1;+0:1])-[C:5](=[O;D1;H0:6])-[O;D1;H1:7] | null | [] | null | null | 20 | HOUR | To a mixture of 5.5 g (14.12 mmol) of 3,5-dibromo-4-methoxy-D-phenylalanine-hydrochloride and 55 ml of methanol were added 150 ml of a saturated methanolic hydrogen chloride solution and the mixture was stirred for 20 hours at room temperature. The residue remaining after evaporation of the solvent was stirred with 50 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Methanol | Secondary amine | null | null | c1ccccc1 | HO- | ClCCl.C(C)(=O)OCC.C1CCCCC1.CO | null | 20 | CO.COc1c(Br)cc(C[C@@H](N)C(=O)O)cc1Br>ClCCl.C(C)(=O)OCC.C1CCCCC1.CO>CN[C@H](Cc1cc(Br)c(OC)c(Br)c1)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1a6e715cfecd4e3a803bf7a5a91ec135 | Clc1ccnc(Cl)n1.c1ccc(CN2CCNCC2)cc1>>Clc1nccc(N2CCN(Cc3ccccc3)CC2)n1 | C([O-])([O-])=O.[K+].[K+].ClC1=NC=CC(=N1)Cl.C1(=CC=CC=C1)CN1CCNCC1>>ClC1=NC=CC(=N1)N1CCN(CC1)CC1=CC=CC=C1 | Cl[c:6]1[cH:5][cH:4][n:3][c:2]([Cl:1])[n:20]1.[NH:7]1[CH2:8][CH2:9][N:10]([CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[CH2:18][CH2:19]1>>[Cl:1][c:2]1[n:3][cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[CH2:18][CH2:19]2)[n:20]1 | Clc1ccnc(Cl)n1.c1ccc(CN2CCNCC2)cc1 | Clc1nccc(N2CCN(Cc3ccccc3)CC2)n1 | null | null | O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 89a9e7e1366d55004dcd9e6694ddaa661145a78e26c30f61d46c470b984e6100 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(CN2CCN(c3ccncn3)CC2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1.[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[Cl;D1;H0:4]-[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:11]2-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-2):[c:7]:[c:6]:[#7;a:5]:1 | null | [] | 40 | CELSIUS | null | null | A mixture of 9.9 g (0.0664 mol) of 2,4-dichloropyrimidine, 200 ml of water and 11.7 ml (0.0673 mol) of 1-(phenylmethyl)piperazine was heated to 40° C. for 2 hours in an ultrasound bath. After cooling the mixture was made alkaline with potassium carbonate and extracted thoroughly with ethyl acetate. The crude product ob... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1cncnc1.C1CNCC[NH]1 | c1cncnc1.C1C[NH]CC[NH]1 | c1cncnc1.C1C[NH]CC[NH]1.c1ccccc1 | HCl | O | 40 | null | Clc1ccnc(Cl)n1.c1ccc(CN2CCNCC2)cc1>O>Clc1nccc(N2CCN(Cc3ccccc3)CC2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d5eced98e88047eaa4bbdc008c01c5b9 | Clc1nccc(N2CCN(Cc3ccccc3)CC2)n1>>c1cc(N2CCNCC2)ncn1 | ClC1=NC=CC(=N1)N1CCN(CC1)CC1=CC=CC=C1.[H][H]>>N1=CN=C(C=C1)N1CCNCC1 | Cl[c:11]1[n:10][c:3]([N:4]2[CH2:5][CH2:6][N:7](Cc3ccccc3)[CH2:8][CH2:9]2)[cH:2][cH:1][n:12]1>>[cH:1]1[cH:2][c:3]([N:4]2[CH2:5][CH2:6][NH:7][CH2:8][CH2:9]2)[n:10][cH:11][n:12]1 | Clc1nccc(N2CCN(Cc3ccccc3)CC2)n1 | c1cc(N2CCNCC2)ncn1 | null | [Pd] | C(C)O | Deprotection | OtherReaction | 36956beecad45c99c9837214f3d1d5ae230ae130997b81662afacce6c3a77353 | 1c2495fab43afd53fc03b1098e2211ccfcbe4ad2bea8ca5d2b8fbd53e59ff1e2 | c1cc(N2CCNCC2)ncn1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#7:4]1-[C:5]-[C:6]-[N;H0;D3;+0:7](-C-c2:c:c:c:c:c:2)-[C:8]-[C:9]-1):[#7;a:10]:[c:11]>>[c:11]:[#7;a:10]:[cH;D2;+0:1]:[#7;a:2]:[c:3]-[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1 | null | [] | null | null | null | null | A solution of 7.4 g (0.0256 mol) of 1-(2-chloro-4-pyrimidinyl)-4-(phenylmethyl)piperazine in 100 ml of ethanol was hydrogenated in the presence of 2 g of 10% palladium/charcoal for 4 hours at 40° C. under 5 bar of hydrogen pressure. The crude product obtained after conventional working up was purified by column chromat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amine | Secondary amine | c1cncnc1.C1C[NH]CC[NH]1.c1ccccc1 | c1cncnc1.C1C[NH]CCN1 | c1cncnc1.C1C[NH]CCN1 | HCl | [Pd].C(C)O | null | null | Clc1nccc(N2CCN(Cc3ccccc3)CC2)n1>[Pd].C(C)O>c1cc(N2CCNCC2)ncn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fc0ea97ec14f4862b0691b9ddf7c80bc | CC(C)(C)OC(=O)N[C@H](Cc1cc(Br)c(N)c(Br)c1)C(=O)O.c1cc(N2CCNCC2)ncn1>>CC(C)(C)OC(=O)N[C@H](Cc1cc(Br)c(N)c(Br)c1)C(=O)N1CCN(c2ccncn2)CC1 | NC1=C(C=C(C[C@@H](NC(=O)OC(C)(C)C)C(=O)O)C=C1Br)Br.N1=CN=C(C=C1)N1CCNCC1.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.[B-](F)(F)(F)F>>NC1=C(C=C(C[C@@H](NC(=O)OC(C)(C)C)C(=O)N2CCN(CC2)C2=NC=NC=C2)C=C1Br)Br | O[C:20]([C@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:10][c:11]1[cH:12][c:13]([Br:14])[c:15]([NH2:16])[c:17]([Br:18])[cH:19]1)=[O:21].[NH:22]1[CH2:23][CH2:24][N:25]([c:26]2[cH:27][cH:28][n:29][cH:30][n:31]2)[CH2:32][CH2:33]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]([CH2:10][c... | CC(C)(C)OC(=O)N[C@H](Cc1cc(Br)c(N)c(Br)c1)C(=O)O.c1cc(N2CCNCC2)ncn1 | CC(C)(C)OC(=O)N[C@H](Cc1cc(Br)c(N)c(Br)c1)C(=O)N1CCN(c2ccncn2)CC1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ed26ef5eea92a0cc433b3f89a34f4c61724425fa15a9d0ec83a0f7a903eec831 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(CCc1ccccc1)N1CCN(c2ccncn2)CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12].[#7:13]1-[C:14]-[C:15]-[NH;D2;+0:16]-[C:17]-[C:18]-1>>[C:4]-[C:3](-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:... | 92 | [{"value": 92.0, "product": "NC1=C(C=C(C[C@@H](NC(=O)OC(C)(C)C)C(=O)N2CCN(CC2)C2=NC=NC=C2)C=C1Br)Br", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared analogously to Example A15a) from 4-amino-3,5-dibromo-N-(1,1-dimethylethoxycarbonyl)-D-phenylalanine and 1-(4-pyrimidinyl)piperazine in the presence of TBTU in a yield of 92% of theory. Colourless, amorphous substance, Rf=0.42 (FM4; Macherey-Nagel POLYGRAM® SIL G/UV254, ready-made films for TLC).
Conditions: S... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1cncnc1 | HO- | null | null | null | CC(C)(C)OC(=O)N[C@H](Cc1cc(Br)c(N)c(Br)c1)C(=O)O.c1cc(N2CCNCC2)ncn1>>CC(C)(C)OC(=O)N[C@H](Cc1cc(Br)c(N)c(Br)c1)C(=O)N1CCN(c2ccncn2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c00cc16f988a402c9a9a388ee7e4d472 | CCOC(=O)C(CC(=O)OC(C)(C)C)(Cc1cn(C)c2ccccc12)C(=O)OCC>>CCOC(=O)C(CC(=O)O)(Cc1cn(C)c2ccccc12)C(=O)OCC | C(C)OC(=O)C(CC(=O)OC(C)(C)C)(CC1=CN(C2=CC=CC=C12)C)C(=O)OCC.FC(C(=O)O)(F)F.C(C)(C)OC(C)C>>C(C)OC(=O)C(CC(=O)O)(CC1=CN(C2=CC=CC=C12)C)C(=O)OCC | CC(C)(C)[O:10][C:8]([CH2:7][C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([CH2:11][c:12]1[cH:13][n:14]([CH3:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]12)[C:22](=[O:23])[O:24][CH2:25][CH3:26])=[O:9]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH2:7][C:8](=[O:9])[OH:10])([CH2:11][c:12]1[cH:13][n:14]([CH3:15])[c:16]2[cH:17][cH:18... | CCOC(=O)C(CC(=O)OC(C)(C)C)(Cc1cn(C)c2ccccc12)C(=O)OCC | CCOC(=O)C(CC(=O)O)(Cc1cn(C)c2ccccc12)C(=O)OCC | null | null | ClCCl | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | c1ccc2[nH]ccc2c1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 63.5 | [{"value": 63.5, "product": "C(C)OC(=O)C(CC(=O)O)(CC1=CN(C2=CC=CC=C12)C)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Produced analogously to Example A1b) from tert.-butyl β,β-bis-(ethoxycarbonyl)-1-methyl-1H-indol-3-butanoate through the action of trifluoroacetic acid in dichloromethane in a yield of 63.5% of theory. Colourless crystals of Mp. 127-130° C. (diisopropylether).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | c1c[nH]c2ccccc12 | Other | ClCCl | null | null | CCOC(=O)C(CC(=O)OC(C)(C)C)(Cc1cn(C)c2ccccc12)C(=O)OCC>ClCCl>CCOC(=O)C(CC(=O)O)(Cc1cn(C)c2ccccc12)C(=O)OCC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4f1d129dbe6d4476bd756c76a8530717 | CCOC(=O)C(CC(=O)OC(C)(C)C)C(=O)OCC.Cc1cc(C)cc(CBr)c1>>CCOC(=O)C(CC(=O)OC(C)(C)C)(Cc1cc(C)cc(C)c1)C(=O)OCC | C(CC(O)(C(=O)O)CC(=O)O)(=O)O.CC=1C=C(CBr)C=C(C1)C.CC(C)(OC(=O)CC(C(=O)OCC)C(=O)OCC)C.[H-].[Na+]>>C(C)OC(=O)C(CC(=O)OC(C)(C)C)(CC1=CC(=CC(=C1)C)C)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][C:8](=[O:9])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[C:24](=[O:25])[O:26][CH2:27][CH3:28].Br[CH2:15][c:16]1[cH:17][c:18]([CH3:19])[cH:20][c:21]([CH3:22])[cH:23]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH2:7][C:8](=[O:9])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])([CH2:15][... | CCOC(=O)C(CC(=O)OC(C)(C)C)C(=O)OCC.Cc1cc(C)cc(CBr)c1 | CCOC(=O)C(CC(=O)OC(C)(C)C)(Cc1cc(C)cc(C)c1)C(=O)OCC | null | null | O1CCCC1.O | C-C Coupling | OtherReaction | 8175b6573d6439ec7ccc45bf6b48843ab56b46dccfc6504384c4766d09f35cc7 | d1817e44576d3a158547867a56245217a593d4f828a6d6dfaa8ed11276894e44 | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH;D3;+0:9](-[C:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C;D1;H3:17])-[C:18](=[O;D1;H0:19])-[#8:20]-[C:21]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C;H0;D4;+0:9](-[C:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14](-[C;D1;H3:15])(-[... | null | [] | null | null | 30 | MINUTE | To a solution of 13.8 g (50.2 mMol) of diethyl [(1,1-dimethyl-ethoxycarbonyl)methyl]-malonoate in 400 ml of anhydrous tetrahydrofuran, 2.3 g (52.7 mMol) of sodium hydride was added whilst being externally cooled with iced water. After stirring for 30 minutes, and maintaining a reaction temperature of 0 to +5° C., the s... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester | Ester.Ester | null | null | c1ccccc1 | HBr | O1CCCC1.O | null | 0.5 | CCOC(=O)C(CC(=O)OC(C)(C)C)C(=O)OCC.Cc1cc(C)cc(CBr)c1>O1CCCC1.O>CCOC(=O)C(CC(=O)OC(C)(C)C)(Cc1cc(C)cc(C)c1)C(=O)OCC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-213a90da85ac41e99b4d8aec0ae0a94d | CC(C)(C)c1ccc(CBr)cc1.CCOC(=O)C(CC(=O)OCc1ccccc1)C(=O)OCC>>CCOC(=O)C(CC(=O)OCc1ccccc1)(Cc1ccc(C(C)(C)C)cc1)C(=O)OCC | C(C)OC(C(C(=O)OCC)CC(=O)OCC1=CC=CC=C1)=O.CC(C)(C)C1=CC=C(CBr)C=C1.[H-].[Na+]>>C1(=CC=CC=C1)COC(CC(CC1=CC=C(C=C1)C(C)(C)C)(C(=O)OCC)C(=O)OCC)=O | Br[CH2:18][c:19]1[cH:20][cH:21][c:22]([C:23]([CH3:24])([CH3:25])[CH3:26])[cH:27][cH:28]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][C:8](=[O:9])[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[C:29](=[O:30])[O:31][CH2:32][CH3:33]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH2:7][C:8](=[O:9])[O:10][CH2:11][c:... | CC(C)(C)c1ccc(CBr)cc1.CCOC(=O)C(CC(=O)OCc1ccccc1)C(=O)OCC | CCOC(=O)C(CC(=O)OCc1ccccc1)(Cc1ccc(C(C)(C)C)cc1)C(=O)OCC | null | null | null | C-C Coupling | OtherReaction | 8175b6573d6439ec7ccc45bf6b48843ab56b46dccfc6504384c4766d09f35cc7 | d1817e44576d3a158547867a56245217a593d4f828a6d6dfaa8ed11276894e44 | O=C(CCCc1ccccc1)OCc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C:9]-[CH;D3;+0:10](-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14])-[C:15](=[O;D1;H0:16])-[#8:17]-[C:18]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C:9]-[C;H0;D4;+0:10](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])(-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14])-[C:15](=[O;D1;H0:16])-[... | 53 | [{"value": 53.0, "product": "C1(=CC=CC=C1)COC(CC(CC1=CC=C(C=C1)C(C)(C)C)(C(=O)OCC)C(=O)OCC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared analogously to Example A62 from diethyl[(phenylmethoxycarbonyl)methyl]-malonoate and 4-(1,1-dimethylethyl)-benzylbromide in the presence of sodium hydride in a yield of 53% of theory.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester | Ester.Ester | null | null | c1ccccc1.c1ccccc1 | HBr | null | null | null | CC(C)(C)c1ccc(CBr)cc1.CCOC(=O)C(CC(=O)OCc1ccccc1)C(=O)OCC>>CCOC(=O)C(CC(=O)OCc1ccccc1)(Cc1ccc(C(C)(C)C)cc1)C(=O)OCC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0794e5dbfbc54addb76c727c8bea4fd9 | CC(C)(C)OC(=O)N1CCNCC1.CN1CCNCC1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>>CN1CCN(C(=O)N2CCN(C(=O)OC(C)(C)C)CC2)CC1 | CC(C)(OC(=O)N1CCNCC1)C.CCN(C(C)C)C(C)C.ClC(Cl)(OC(OC(Cl)(Cl)Cl)=O)Cl.CN1CCNCC1.CCN(C(C)C)C(C)C>>CC(C)(OC(=O)N1CCN(CC1)C(=O)N1CCN(CC1)C)C | [NH:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]1.[CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:21][CH2:22]1.ClC(Cl)(Cl)O[C:6](OC(Cl)(Cl)Cl)=[O:7]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[N:8]2[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:1... | CC(C)(C)OC(=O)N1CCNCC1.CN1CCNCC1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl | CN1CCN(C(=O)N2CCN(C(=O)OC(C)(C)C)CC2)CC1 | null | null | ClCCl | Acylation | OtherReaction | ae4f48befa687177dfeed5928c229a44d13cdf3242774c0974b6cd3c5288631f | c77dcb628c46f34db12abe282042119a29544ea9236aafae076c5fc9c8355903 | O=C(N1CCNCC1)N1CCNCC1 | Cl-C(-Cl)(-Cl)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-C(-Cl)(-Cl)-Cl.[#7:3]1-[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]-1.[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:12]1-[C:11]-[C:10]-[#7:9]-[C:14]-[C:13]-1)-[N;H0;D3;+0:6]1-[C:7]-[C:8]-[#7:3]-[C:4]-[C:5]-1 | null | [] | null | null | null | null | To a solution of 1.1 g of triphosgene (3.7 mMol) in 20 ml of dichloromethane, a mixture of 1.2 g (10 mMol) of 1-methyl-piperazine, 0.38 ml (22 mMol) of DIEA and 35 ml of dichloromethane was added dropwise at room temperature within 30 minutes, and then the solution of 1.9 g (10 mMol) of 1-(1,1-dimethyl-ethoxycarbonyl)p... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Trichloro group.Carbonic Ester.Secondary amine.Secondary amine | Urea | C1CNCC[NH]1.C1C[NH]CCN1 | C1C[NH]CC[NH]1.C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.C1C[NH]CC[NH]1 | HCl | ClCCl | null | null | CC(C)(C)OC(=O)N1CCNCC1.CN1CCNCC1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>ClCCl>CN1CCN(C(=O)N2CCN(C(=O)OC(C)(C)C)CC2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6be8b56fd9e14b818339871c69e0b549 | CNC.O=C(O)CCC(=O)c1ccc(F)cc1>>CN(C)C(=O)CCC(=O)c1ccc(F)cc1 | CNC.FC1=CC=C(C=C1)C(CCC(=O)O)=O>>CN(C(CCC(C1=CC=C(C=C1)F)=O)=O)C | [CH3:1][NH:2][CH3:3].O[C:4](=[O:5])[CH2:6][CH2:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]1>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[CH2:6][CH2:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]([F:14])[cH:15][cH:16]1 | CNC.O=C(O)CCC(=O)c1ccc(F)cc1 | CN(C)C(=O)CCC(=O)c1ccc(F)cc1 | null | null | O1CCCC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[C:5]=[O;D1;H0:6].[C;D1;H3:7]-[NH;D2;+0:8]-[C;D1;H3:9]>>[C;D1;H3:7]-[N;H0;D3;+0:8](-[C;D1;H3:9])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[C:5]=[O;D1;H0:6] | null | [] | null | null | 2.5 | HOUR | To a solution of 30.5 g (0.155 Mol) of 4-fluoro-γ-oxobenzenebutanoic acid in 470 ml tetrahydrofuran, 35.0 g (0.216 Mol) of N,N′-carbonyldiimidazole was added with stirring and at room temperature and held at room temperature for a further 2.5 hours. Then, 13.7 g (0.304 Mol) of dimethylamine was added under strong exter... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccccc1 | HO- | O1CCCC1 | null | 2.5 | CNC.O=C(O)CCC(=O)c1ccc(F)cc1>O1CCCC1>CN(C)C(=O)CCC(=O)c1ccc(F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b8fc1a4764f84eaca83de04dc57dc356 | CN(C)C(=O)CCC(=O)c1ccc(F)cc1.c1ccc(CN2CCNCC2)cc1>>CN(C)C(=O)CCC(=O)c1ccc(N2CCN(Cc3ccccc3)CC2)cc1 | C1(=CC=CC=C1)CN1CCNCC1.CN(C(CCC(C1=CC=C(C=C1)F)=O)=O)C.C1(=CC=CC=C1)CN1CCNCC1.CCN(C(C)C)C(C)C.N.C(C)(C)OC(C)C>>CN(C(CCC(C1=CC=C(C=C1)N1CCN(CC1)CC1=CC=CC=C1)=O)=O)C | F[c:13]1[cH:12][cH:11][c:10]([C:8]([CH2:7][CH2:6][C:4]([N:2]([CH3:1])[CH3:3])=[O:5])=[O:9])[cH:28][cH:27]1.[NH:14]1[CH2:15][CH2:16][N:17]([CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[CH2:25][CH2:26]1>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[CH2:6][CH2:7][C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]([N:14]2[CH2:15][CH2:16... | CN(C)C(=O)CCC(=O)c1ccc(F)cc1.c1ccc(CN2CCNCC2)cc1 | CN(C)C(=O)CCC(=O)c1ccc(N2CCN(Cc3ccccc3)CC2)cc1 | null | null | ClCCl.ClCCl.CO | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 75de53007ec0cb91435746fdefbf3b121f745fc71ddebd19c6e45a5212b3f56a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(CN2CCN(c3ccccc3)CC2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | null | [] | null | null | null | null | The mixture of 33.48 g (0.15 Mol) of N,N-dimethyl-4-fluoro-γ-oxobenzenebutanoic acid amide, 29.6 g (0.168 Mol) of 1-(phenyl-methyl)piperazine and 6 ml of DIEA was refluxed for 6 hours. Another 30 g (0.17 Mol) of (phenylmethyl)piperazine was added, and the mixture was refluxed for a further 7 hours. The mixture was take... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CNCC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | HF | ClCCl.ClCCl.CO | null | null | CN(C)C(=O)CCC(=O)c1ccc(F)cc1.c1ccc(CN2CCNCC2)cc1>ClCCl.ClCCl.CO>CN(C)C(=O)CCC(=O)c1ccc(N2CCN(Cc3ccccc3)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a34a7206ec6d4187a9d8e2d9e29d451e | CN(C)C(=O)CCC(=O)c1ccc(N2CCN(Cc3ccccc3)CC2)cc1>>CN(C)CCCC(O)c1ccc(N2CCN(Cc3ccccc3)CC2)cc1 | CN(C(CCC(C1=CC=C(C=C1)N1CCN(CC1)CC1=CC=CC=C1)=O)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>CN(CCCC(O)C1=CC=C(C=C1)N1CCN(CC1)CC1=CC=CC=C1)C | O=[C:4]([N:2]([CH3:1])[CH3:3])[CH2:5][CH2:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([N:13]2[CH2:14][CH2:15][N:16]([CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[CH2:24][CH2:25]2)[cH:26][cH:27]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][CH:7]([OH:8])[c:9]1[cH:10][cH:11][c:12]([N:13]2[CH2:14][CH2:15][N:16]([CH2:1... | CN(C)C(=O)CCC(=O)c1ccc(N2CCN(Cc3ccccc3)CC2)cc1 | CN(C)CCCC(O)c1ccc(N2CCN(Cc3ccccc3)CC2)cc1 | null | null | C(C)(=O)OCC.CO | Reduction | OtherReaction | b9e615d9787ce0171ee061de926a9a6c4a1436df6786dca9312d5e905f2cc272 | 519f788b494414b16d92f14899fd2ea05d5c55e163150098e770ae659993e4b1 | c1ccc(CN2CCN(c3ccccc3)CC2)cc1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3]-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-[c:6](:[c:7]):[c:8])-[#7:9](-[C;D1;H3:10])-[C;D1;H3:11]>>[C;D1;H3:10]-[#7:9](-[C;D1;H3:11])-[CH2;D2;+0:1]-[C:2]-[C:3]-[CH;D3;+0:4](-[OH;D1;+0:5])-[c:6](:[c:7]):[c:8] | 61 | [{"value": 61.0, "product": "CN(CCCC(O)C1=CC=C(C=C1)N1CCN(CC1)CC1=CC=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared analogously to example A51 from N,N-dimethyl-γ-oxo-4-[4-(phenylmethyl)-1-piperazinyl]-benzenebutanoic acid amide by reduction with lithium aluminium hydride in a yield of 61% of theory. Colourless, amorphous substance of Rf=0.62 (eluant:ethyl acetate/methanol 1/1 v/v).
Conditions: See reaction.notes.procedure_... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Tertiary amide | Secondary alcohol | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | Other | C(C)(=O)OCC.CO | null | null | CN(C)C(=O)CCC(=O)c1ccc(N2CCN(Cc3ccccc3)CC2)cc1>C(C)(=O)OCC.CO>CN(C)CCCC(O)c1ccc(N2CCN(Cc3ccccc3)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-18dba26e8e8948fd939be7197b40dddb | CN(C)CCCC(O)c1ccc(N2CCN(Cc3ccccc3)CC2)cc1>>CN(C)CCCCc1ccc(N2CCNCC2)cc1.Cl | CN(CCCC(O)C1=CC=C(C=C1)N1CCN(CC1)CC1=CC=CC=C1)C.Cl>>Cl.Cl.CN(CCCCC1=CC=C(C=C1)N1CCNCC1)C | O[CH:7]([CH2:6][CH2:5][CH2:4][N:2]([CH3:1])[CH3:3])[c:8]1[cH:9][cH:10][c:11]([N:12]2[CH2:13][CH2:14][N:15](Cc3ccccc3)[CH2:16][CH2:17]2)[cH:18][cH:19]1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]([N:12]2[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]2)[cH:18][cH:19]1.[ClH:21] | CN(C)CCCC(O)c1ccc(N2CCN(Cc3ccccc3)CC2)cc1 | CN(C)CCCCc1ccc(N2CCNCC2)cc1.Cl | null | [Pd] | C(C)(=O)OCC.CO | Miscellaneous | OtherReaction | 27ebccc6bd7398aed33c14603124fad0a2a9830f2fd95e0c1c7d8a07030bc61f | 4599f2286febf0d7865561d62c4ee648c5816b4922994088b3d624b8a0c5602f | c1ccc(N2CCNCC2)cc1 | C(-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1)-c1:c:c:c:c:c:1.O-[CH;D3;+0:7](-[C:8]-[C:9])-[c:10](:[c:11]):[c:12]>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1.[C:9]-[C:8]-[CH2;D2;+0:7]-[c:10](:[c:11]):[c:12] | null | [] | null | null | null | null | Prepared analogously to example A20b) from 4-[4-[4-(dimethylamino)-1-hydroxybutyl]phenyl]-1-(phenylmethyl)piperazine by catalytic hydrogenation in the presence of palladium/charcoal and hydrochloric acid in a quantitative yield. Colourless, amorphous substance of Rf=0.37 (eluant:ethyl acetate/methanol 50/50/0.5 v/v/v).... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Tertiary amine | Secondary amine | C1C[NH]CC[NH]1.c1ccccc1 | C1C[NH]CCN1 | c1ccccc1.C1C[NH]CCN1 | HO- | [Pd].C(C)(=O)OCC.CO | null | null | CN(C)CCCC(O)c1ccc(N2CCN(Cc3ccccc3)CC2)cc1>[Pd].C(C)(=O)OCC.CO>CN(C)CCCCc1ccc(N2CCNCC2)cc1.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-502a4dac111a47e0a112588a9c43aa78 | COc1ccccc1CN.N[C@H](Cc1cc(Br)c(O)c(Br)c1)C(=O)N[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)N1CCN(c2ccncc2)CC1>>COc1ccccc1CNC(=O)NC(Cc1cc(Br)c(O)c(Br)c1)C(=O)N[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)N1CCN(c2ccncc2)CC1 | COC1=C(C=CC=C1)CN.BrC=1C=C(C[C@@H](N)C(=O)N[C@@H](CCCCNC(=O)OCC2=CC=CC=C2)C(=O)N2CCN(CC2)C2=CC=NC=C2)C=C(C1O)Br.O1CCCC1.O1CCCC1>>BrC=1C=C(CC(NC(=O)NCC2=C(C=CC=C2)OC)C(=O)N[C@@H](CCCCNC(=O)OCC2=CC=CC=C2)C(=O)N2CCN(CC2)C2=CC=NC=C2)C=C(C1O)Br | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][NH2:10].[NH2:13][C@H:14]([CH2:15][c:16]1[cH:17][c:18]([Br:19])[c:20]([OH:21])[c:22]([Br:23])[cH:24]1)[C:25](=[O:26])[NH:27][C@@H:28]([CH2:29][CH2:30][CH2:31][CH2:32][NH:33][C:34](=[O:35])[O:36][CH2:37][c:38]1[cH:39][cH:40][cH:41][cH:42][cH:43]1)[C:44](=[O:45])[N:4... | COc1ccccc1CN.N[C@H](Cc1cc(Br)c(O)c(Br)c1)C(=O)N[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)N1CCN(c2ccncc2)CC1 | COc1ccccc1CNC(=O)NC(Cc1cc(Br)c(O)c(Br)c1)C(=O)N[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)N1CCN(c2ccncc2)CC1 | null | null | null | Acylation | OtherReaction | 0803607fba0d95b5aa54f50a0ea365a82edda165361e01ad9e7ff57568bb8df0 | 4ff96020857e85930fbee987c7fa4ef615e45b2ea39cff27ceaec8f9174d5b6f | O=C(NCc1ccccc1)NC(Cc1ccccc1)C(=O)N[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)N1CCN(c2ccncc2)CC1 | [#7:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#7:5]-[C:6](=[O;D1;H0:7])-[C@H;D3;+0:8](-[NH2;D1;+0:9])-[C:10]-[c:11].[NH2;D1;+0:12]-[C:13]-[c:14]>>[#7:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#7:5]-[C:6](=[O;D1;H0:7])-[CH;D3;+0:8](-[C:10]-[c:11])-[NH;D2;+0:9]-[C:15](=[O;D1;H0:16])-[NH;D2;+0:12]-[C:13]-[c:14] | null | [] | -10 | CELSIUS | null | null | A tetrahydrofuran solution (50 ml) of 1.0 g (1.34 mmol) of 1-[N2-(3,5-dibromo-D-tyrosyl)-N6-(phenylmethoxycarbonyl)-L-lysyl]-4-(4-pyridinyl)-piperazine was added dropwise over a period of 40 minutes to a suspension of 0.33 g (2.01 mmol) of CDT in 50 ml of tetrahydrofuran cooled to −10 ° C. and stirred. The reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine | Urea | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | Other | null | -10 | null | COc1ccccc1CN.N[C@H](Cc1cc(Br)c(O)c(Br)c1)C(=O)N[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)N1CCN(c2ccncc2)CC1>>COc1ccccc1CNC(=O)NC(Cc1cc(Br)c(O)c(Br)c1)C(=O)N[C@@H](CCCCNC(=O)OCc1ccccc1)C(=O)N1CCN(c2ccncc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6bc6d39ce0d2490a84430efd397273ce | COc1ccc(OC)c(CCNC(=O)N[C@H](Cc2cc(Br)c(O)c(Br)c2)C(=O)N[C@@H](CCCCNC(=O)OCc2ccccc2)C(=O)N2CCN(c3ccncc3)CC2)c1>>COc1ccc(OC)c(CCNC(=O)NC(Cc2cc(Br)c(O)c(Br)c2)C(=O)N[C@@H](CCCCN)C(=O)N2CCN(c3ccncc3)CC2)c1 | C(C)OCC.COC1=C(C=C(C=C1)OC)CCNC(=O)N[C@H](CC1=CC(=C(C(=C1)Br)O)Br)C(=O)N[C@@H](CCCCNC(=O)OCC1=CC=CC=C1)C(=O)N1CCN(CC1)C1=CC=NC=C1.Br>>COC1=C(C=C(C=C1)OC)CCNC(=O)NC(CC1=CC(=C(C(=C1)Br)O)Br)C(=O)N[C@@H](CCCCN)C(=O)N1CCN(CC1)C1=CC=NC=C1 | O=C(OCc1ccccc1)[NH:35][CH2:34][CH2:33][CH2:32][CH2:31][C@H:30]([NH:29][C:27]([C@H:16]([NH:15][C:13]([NH:12][CH2:11][CH2:10][c:9]1[c:6]([O:7][CH3:8])[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:50]1)=[O:14])[CH2:17][c:18]1[cH:19][c:20]([Br:21])[c:22]([OH:23])[c:24]([Br:25])[cH:26]1)=[O:28])[C:36](=[O:37])[N:38]1[CH2:39][CH2:40][N... | COc1ccc(OC)c(CCNC(=O)N[C@H](Cc2cc(Br)c(O)c(Br)c2)C(=O)N[C@@H](CCCCNC(=O)OCc2ccccc2)C(=O)N2CCN(c3ccncc3)CC2)c1 | COc1ccc(OC)c(CCNC(=O)NC(Cc2cc(Br)c(O)c(Br)c2)C(=O)N[C@@H](CCCCN)C(=O)N2CCN(c3ccncc3)CC2)c1 | null | null | C1(=CC=CC=C1)OC.C(C)(=O)O | Reduction | Hydrogenolysis of amides/imides/carbamates | 087b6600ba91d3df931fe6979f2445c192cbfd59e04fd2d8a10f7c7573ac669f | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | O=C(NCCc1ccccc1)NC(Cc1ccccc1)C(=O)NCC(=O)N1CCN(c2ccncc2)CC1 | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | 12 | HOUR | A mixture of 0.8 g (0.84 mmol) of 1-[N2—[N-[[[2-(2,5-dimethoxyphenyl)ethyl]amino]carbonyl]-3,5-dibromo-D-tyrosyl]-N6-[(phenylmethoxy)carbonyl]-L-lysyl]-4-(4-pyridinyl)-piperazine, 50 ml of glacial acetic acid, 25 ml of a 33% solution of hydrogen bromide in glacial acetic acid and 2 ml of anisole was stirred for 12 hour... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccccc1 | null | c1ccccc1.c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | HO- | C1(=CC=CC=C1)OC.C(C)(=O)O | null | 12 | COc1ccc(OC)c(CCNC(=O)N[C@H](Cc2cc(Br)c(O)c(Br)c2)C(=O)N[C@@H](CCCCNC(=O)OCc2ccccc2)C(=O)N2CCN(c3ccncc3)CC2)c1>C1(=CC=CC=C1)OC.C(C)(=O)O>COc1ccc(OC)c(CCNC(=O)NC(Cc2cc(Br)c(O)c(Br)c2)C(=O)N[C@@H](CCCCN)C(=O)N2CCN(c3ccncc3)CC2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-55f41c892ab54a1eb0c91988fb9eb7a7 | CC(C)(C)OC(=O)N1CCC(C2CCNCC2)CC1.Nc1c(Br)cc(C[C@@H](NC(=O)OCC2c3ccccc3-c3ccccc32)C(=O)O)cc1Br>>CC(C)(C)OC(=O)N1CCC(C2CCN(C(=O)[C@H](N)Cc3cc(Br)c(N)c(Br)c3)CC2)CC1 | C(C)NCC.NC1=C(C=C(C[C@@H](NC(=O)OCC2C3=CC=CC=C3C=3C=CC=CC23)C(=O)O)C=C1Br)Br.C=1C=CC2=C(C1)N=NN2O.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.CC(C)(OC(=O)N1CCC(CC1)C1CCNCC1)C>>NC1=C(C=C(C[C@@H](N)C(=O)N2CCC(CC2)C2CCN(CC2)C(=O)OC(C)(C)C)C=C1Br)Br | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([CH:12]2[CH2:13][CH2:14][NH:15][CH2:30][CH2:31]2)[CH2:32][CH2:33]1.O=C(OCC1c2ccccc2-c2ccccc21)[NH:19][C@@H:18]([C:16](O)=[O:17])[CH2:20][c:21]1[cH:22][c:23]([Br:24])[c:25]([NH2:26])[c:27]([Br:28])[cH:29]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C... | CC(C)(C)OC(=O)N1CCC(C2CCNCC2)CC1.Nc1c(Br)cc(C[C@@H](NC(=O)OCC2c3ccccc3-c3ccccc32)C(=O)O)cc1Br | CC(C)(C)OC(=O)N1CCC(C2CCN(C(=O)[C@H](N)Cc3cc(Br)c(N)c(Br)c3)CC2)CC1 | null | null | O1CCCC1 | Acylation | OtherReaction | 0a0ae8a2ca7400c68713b2eff2f9a2345523782d772c1dedff8e78ccbbbd1e0a | 77a668978e69174334be4f36a3c7053272639f750105af3c4ac3ba22ece7f87c | O=C(CCc1ccccc1)N1CCC(C2CCNCC2)CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[NH;D2;+0:5]-C(=O)-O-C-C1-c2:c:c:c:c:c:2-c2:c:c:c:c:c:2-1.[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[NH2;D1;+0:5])-[C:9]-[C:10] | null | [] | null | null | 2 | HOUR | A mixture of 5.60 g (0.01 mol) of 4-amino-3,5-dibromo-N -(9-fluorenylmethoxycarbonyl)-D-phenylalanine, 1.35 g (0.01 mol) HOBt, 3.21 g (0.01 mol) TBTU, 1.29 g (0.01 mol) DIEA, 2.68 g (0.01 mol) 4-[1-(1,1-dimethylethoxycarbonyl)-4-piperidinyl]-piperidine and 150 ml of tetrahydrofuran was stirred for 2 hours at room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Secondary amine | Tertiary amide.Primary amine | C1CCNCC1.c1ccc2c(c1)Cc1ccccc12 | C1CC[NH]CC1 | C1CC[NH]CC1.C1CC[NH]CC1.c1ccccc1 | HO- | O1CCCC1 | null | 2 | CC(C)(C)OC(=O)N1CCC(C2CCNCC2)CC1.Nc1c(Br)cc(C[C@@H](NC(=O)OCC2c3ccccc3-c3ccccc32)C(=O)O)cc1Br>O1CCCC1>CC(C)(C)OC(=O)N1CCC(C2CCN(C(=O)[C@H](N)Cc3cc(Br)c(N)c(Br)c3)CC2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-81654d5a90fb4625848bcfd5d1a62659 | CC(C)(C)OC(=O)N[C@H](Cc1cc(Br)c(O)c(Br)c1)C(=O)N1CCC(N2CCCCC2)CC1>>CN[C@H](Cc1cc(Br)c(O)c(Br)c1)CN1CCC(N2CCCCC2)CC1 | [H-].[Al+3].[Li+].[H-].[H-].[H-].BrC=1C=C(C[C@@H](NC(=O)OC(C)(C)C)C(=O)N2CCC(CC2)N2CCCCC2)C=C(C1O)Br.[Cl-].[NH4+]>>BrC=1C=C(C=C(C1O)Br)C[C@H](CN1CCC(CC1)N1CCCCC1)NC | CC(C)(C)O[C:1](=O)[NH:2][C@H:3]([CH2:4][c:5]1[cH:6][c:7]([Br:8])[c:9]([OH:10])[c:11]([Br:12])[cH:13]1)[C:14](=O)[N:15]1[CH2:16][CH2:17][CH:18]([N:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[CH2:25][CH2:26]1>>[CH3:1][NH:2][C@H:3]([CH2:4][c:5]1[cH:6][c:7]([Br:8])[c:9]([OH:10])[c:11]([Br:12])[cH:13]1)[CH2:14][N:15]1[CH... | CC(C)(C)OC(=O)N[C@H](Cc1cc(Br)c(O)c(Br)c1)C(=O)N1CCC(N2CCCCC2)CC1 | CN[C@H](Cc1cc(Br)c(O)c(Br)c1)CN1CCC(N2CCCCC2)CC1 | null | null | O1CCCC1 | Reduction | OtherReaction | d1e38ff76373f2f85a70c476a5d7ea2d461bd8feff67e57b568219071b445e34 | e3e848d08b64607479a3af6f757302d1c3f585ca2558bd4bfb2ce28c641ade14 | c1ccc(CCCN2CCC(N3CCCCC3)CC2)cc1 | C-C(-C)(-C)-O-[C;H0;D3;+0:1](=O)-[#7:2]-[C:3](-[C:4])-[C;H0;D3;+0:5](=O)-[#7:6](-[C:7])-[C:8]>>[C:7]-[#7:6](-[CH2;D2;+0:5]-[C:3](-[C:4])-[#7:2]-[CH3;D1;+0:1])-[C:8] | null | [] | null | null | null | null | To a suspension of 2.3 g (60 mmol) lithium aluminium hydride in 100 ml anhydrous tetrahydrofuran, a solution of 11.0 g (18.66 mmol) 1-[3,5-dibromo-N-(1,1-dimethylethoxycarbonyl)-D-tyrosyl]-4-(1-piperidinyl)piperidine in 100 ml anhydrous tetrahydrofuran was added dropwise at room temperature whilst being stirred. It was... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Tertiary amide.Boc | null | null | null | c1ccccc1.C1CC[NH]CC1.C1CC[NH]CC1 | HO- | O1CCCC1 | null | null | CC(C)(C)OC(=O)N[C@H](Cc1cc(Br)c(O)c(Br)c1)C(=O)N1CCC(N2CCCCC2)CC1>O1CCCC1>CN[C@H](Cc1cc(Br)c(O)c(Br)c1)CN1CCC(N2CCCCC2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8d5284a1679a4cf5a3b8e581bbff6cba | CN1CCC(C2CCN(C(=O)[C@@H](Cc3cc(Br)c(N)c(Br)c3)NC(=O)N3CCC(=O)CC3)CC2)CC1.[NH4+]>>CN1CCC(C2CCN(C(=O)[C@@H](Cc3cc(Br)c(N)c(Br)c3)NC(=O)N3CCC(N)CC3)CC2)CC1 | Cl.C(#N)[BH3-].[Na+].NC1=C(C=C(C[C@@H](NC(=O)N2CCC(CC2)=O)C(=O)N2CCC(CC2)C2CCN(CC2)C)C=C1Br)Br.C(C)(=O)[O-].[NH4+]>>NC1=C(C=C(C[C@@H](NC(=O)N2CCC(CC2)N)C(=O)N2CCC(CC2)C2CCN(CC2)C)C=C1Br)Br | O=[C:29]1[CH2:28][CH2:27][N:26]([C:24]([NH:23][C@@H:12]([C:10]([N:9]2[CH2:8][CH2:7][CH:6]([CH:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH2:36][CH2:35]3)[CH2:34][CH2:33]2)=[O:11])[CH2:13][c:14]2[cH:15][c:16]([Br:17])[c:18]([NH2:19])[c:20]([Br:21])[cH:22]2)=[O:25])[CH2:32][CH2:31]1.[NH4+:30]>>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([CH... | CN1CCC(C2CCN(C(=O)[C@@H](Cc3cc(Br)c(N)c(Br)c3)NC(=O)N3CCC(=O)CC3)CC2)CC1.[NH4+] | CN1CCC(C2CCN(C(=O)[C@@H](Cc3cc(Br)c(N)c(Br)c3)NC(=O)N3CCC(N)CC3)CC2)CC1 | null | null | CO | Functional Group Interconversion | OtherReaction | 509132ca3138b69d03bdcf1880a470c57c5201972d576e184fca23f739b2e7de | 2ef9e3e9915394571ec6196ff6ea06bca9f3dff8c6f6f43c81edc876014a94a5 | O=C(N[C@H](Cc1ccccc1)C(=O)N1CCC(C2CCNCC2)CC1)N1CCCCC1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[NH4+;D0:7]>>[NH2;D1;+0:7]-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1 | null | [] | null | null | null | null | 653 mg (10.4 mMol) 95% sodium cyanoborohydride (Aldrich 15.615-9) was stirred into the mixture of 930 mg (1.48 mMol) 1-[4-amino-3,5-dibromo-N-[(4-oxo-1-piperidinyl)carbonyl]-D-phenylalanyl]-4-(1-methyl-4-piperidinyl)-piperidine, 1143 mg (14.8 mMol) ammonium acetate (Merck No. 1115) and 30 ml anhydrous methanol at room ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary amine | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1.C1CC[NH]CC1.c1ccccc1.C1CC[NH]CC1 | HO- | CO | null | null | CN1CCC(C2CCN(C(=O)[C@@H](Cc3cc(Br)c(N)c(Br)c3)NC(=O)N3CCC(=O)CC3)CC2)CC1.[NH4+]>CO>CN1CCC(C2CCN(C(=O)[C@@H](Cc3cc(Br)c(N)c(Br)c3)NC(=O)N3CCC(N)CC3)CC2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4af938b5bcb34c07b5af84808ffa2d71 | COC(=O)CCc1ccc(OCCCCOc2ccccc2)cc1>>OCCCc1ccc(OCCCCOc2ccccc2)cc1 | CO.Cl.[H-].[Al+3].[Li+].[H-].[H-].[H-].O(C1=CC=CC=C1)CCCCOC1=CC=C(C=C1)CCC(=O)OC.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>O(C1=CC=CC=C1)CCCCOC1=CC=C(C=C1)CCCO | CO[C:2](=[O:1])[CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21][cH:22]1>>[OH:1][CH2:2][CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21][cH:22]1 | COC(=O)CCc1ccc(OCCCCOc2ccccc2)cc1 | OCCCc1ccc(OCCCCOc2ccccc2)cc1 | null | null | O1CCCC1.C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(OCCCCOc2ccccc2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | 99.3 | [{"value": 99.3, "product": "O(C1=CC=CC=C1)CCCCOC1=CC=C(C=C1)CCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 20.1 ml of a 1 molar solution of lithium aluminium hydride in tetrahydrofuran is introduced. While stirring, a solution of 12.0 g of methyl 3-[4-(4-phenoxybutoxy)-phenyl]propanoate in 40 ml of THF is added dropwise in such a way that the mixture just starts to boil. The mixture is stirred at room temperature for 30 min... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1ccccc1 | Other | O1CCCC1.C1CCOC1 | null | null | COC(=O)CCc1ccc(OCCCCOc2ccccc2)cc1>O1CCCC1.C1CCOC1>OCCCc1ccc(OCCCCOc2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-93a6c17c3c44457788a844ec68ab49dd | BrCc1ccc(-c2ccccc2)cc1.CCC(O)c1ccc(O)cc1>>OCCCc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1 | C1(=CC=CC=C1)C1=CC=C(CBr)C=C1.OC1=CC=C(C=C1)C(CC)O.C([O-])([O-])=O.[K+].[K+]>>C1(=CC=C(C=C1)COC1=CC=C(C=C1)CCCO)C1=CC=CC=C1 | Br[CH2:10][c:11]1[cH:12][cH:13][c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21][cH:22]1.[OH:1][CH:2]([CH2:3][CH3:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:23][cH:24]1>>[OH:1][CH2:2][CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:21][... | BrCc1ccc(-c2ccccc2)cc1.CCC(O)c1ccc(O)cc1 | OCCCc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1 | null | null | C(CCC)#N | Heteroatom Alkylation and Arylation | OtherReaction | f56d649948cba65c9376a901cec2818e22baedc66717ed77a9ca8353db79693c | 7f64cf79de1de9819f84ad103fb5b7fd8663a5d8aa5dc2723252d02cddf9e9b9 | c1ccc(OCc2ccc(-c3ccccc3)cc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6]-[CH;D3;+0:7](-[O;D1;H1:8])-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12](-[OH;D1;+0:13]):[c:14]:[c:15]:1>>[O;D1;H1:8]-[CH2;D2;+0:7]-[C:6]-[CH2;D2;+0:5]-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12](-[O;H0;D2;+0:13]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:14]:[c:15]:1 | null | [] | null | null | null | null | 12.8 g (41.4 mmol) of 4-phenylbenzyl bromide, 6.94 g (45.6 mmol) of 4-hydroxy-phenylpropanol and 6.87 g (49.7 mmol) of potassium carbonate are stirred in 50 ml of butyronitrile at 120° C. for 6 hours. Cooling to room temperature is followed by removal of the inorganic salts by filtration with suction and concentration ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary alcohol.Aromatic alcohol | Ether.Primary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HBr | C(CCC)#N | null | null | BrCc1ccc(-c2ccccc2)cc1.CCC(O)c1ccc(O)cc1>C(CCC)#N>OCCCc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5e6bafed4c4c4ef8ab93d67c01b0ad1a | COC(=O)C1CCNCC1.COC(=O)c1ccc(O)c(C(=O)O)c1>>COC(=O)c1ccc(O)c(C(=O)N2CCC(C(=O)OC)CC2)c1 | OC1=C(C(=O)O)C=C(C=C1)C(=O)OC.Cl.N1CCC(CC1)C(=O)OC>>OC1=C(C(=O)N2CCC(CC2)C(=O)OC)C=C(C=C1)C(=O)OC | [NH:13]1[CH2:14][CH2:15][CH:16]([C:17](=[O:18])[O:19][CH3:20])[CH2:21][CH2:22]1.O[C:11]([c:10]1[c:8]([OH:9])[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:23]1)=[O:12]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:10]([C:11](=[O:12])[N:13]2[CH2:14][CH2:15][CH:16]([C:17](=[O:18])[O:19][CH3:20])[CH2:21][CH... | COC(=O)C1CCNCC1.COC(=O)c1ccc(O)c(C(=O)O)c1 | COC(=O)c1ccc(O)c(C(=O)N2CCC(C(=O)OC)CC2)c1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | fbfce93ec1ece674255bb96c5cec09ad611382b41cf117dfe580015e21744a71 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1ccccc1)N1CCCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:9]-[C:10] | null | [] | null | null | null | null | Methyl 1-[2-hydroxy-5-(methoxycarbonyl)benzoyl]-4-piperidinecarboxylate is prepared in analogy to the process described in Example IX, method 1, from 2-hydroxy-5-carbomethoxybenzoic acid [CAS No. 79128-78-2] and methyl piperidine-4-carboxylate hydrochloride.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1 | HO- | null | null | null | COC(=O)C1CCNCC1.COC(=O)c1ccc(O)c(C(=O)O)c1>>COC(=O)c1ccc(O)c(C(=O)N2CCC(C(=O)OC)CC2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-71d21d3c4714444f97f2936eaf326634 | COC(=O)C1CCNCC1.COC(=O)c1ccc([N+](=O)[O-])c(C(=O)O)c1>>COC(=O)c1ccc([N+](=O)[O-])c(C(=O)N2CCC(C(=O)OC)CC2)c1 | COC(=O)C=1C=CC(=C(C(=O)O)C1)[N+](=O)[O-].Cl.N1CCC(CC1)C(=O)OC>>COC(=O)C=1C=CC(=C(C(=O)N2CCC(CC2)C(=O)OC)C1)[N+](=O)[O-] | [NH:15]1[CH2:16][CH2:17][CH:18]([C:19](=[O:20])[O:21][CH3:22])[CH2:23][CH2:24]1.O[C:13]([c:12]1[c:8]([N+:9](=[O:10])[O-:11])[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:25]1)=[O:14]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([N+:9](=[O:10])[O-:11])[c:12]([C:13](=[O:14])[N:15]2[CH2:16][CH2:17][CH:18]([C:19](=[... | COC(=O)C1CCNCC1.COC(=O)c1ccc([N+](=O)[O-])c(C(=O)O)c1 | COC(=O)c1ccc([N+](=O)[O-])c(C(=O)N2CCC(C(=O)OC)CC2)c1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | fbfce93ec1ece674255bb96c5cec09ad611382b41cf117dfe580015e21744a71 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1ccccc1)N1CCCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:9]-[C:10] | null | [] | null | null | null | null | Methyl 1-[5-(methoxycarbonyl)-2-nitrobenzoyl]-4-piperidinecarboxylate is prepared in analogy to the process described in Example IX from 5-(methoxycarbonyl)-2-nitrobenzoic acid and methyl piperidine-4-carboxylate hydrochloride.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1 | HO- | null | null | null | COC(=O)C1CCNCC1.COC(=O)c1ccc([N+](=O)[O-])c(C(=O)O)c1>>COC(=O)c1ccc([N+](=O)[O-])c(C(=O)N2CCC(C(=O)OC)CC2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6ed629ecbb44458f9e3723db1e524f27 | BrCCCc1ccc(OCCCCOc2ccccc2)cc1.CCOC(=O)c1ccc(O)c(C=O)c1>>CCOC(=O)c1ccc(OCCCc2ccc(OCCCCOc3ccccc3)cc2)c(C=O)c1 | BrCCCC1=CC=C(C=C1)OCCCCOC1=CC=CC=C1.C(=O)C=1C=C(C(=O)OCC)C=CC1O.C([O-])([O-])=O.[K+].[K+]>>C(=O)C=1C=C(C(=O)OCC)C=CC1OCCCC1=CC=C(C=C1)OCCCCOC1=CC=CC=C1 | Br[CH2:11][CH2:12][CH2:13][c:14]1[cH:15][cH:16][c:17]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[cH:30][cH:31]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([OH:10])[c:32]([CH:33]=[O:34])[cH:35]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([O:10][CH2... | BrCCCc1ccc(OCCCCOc2ccccc2)cc1.CCOC(=O)c1ccc(O)c(C=O)c1 | CCOC(=O)c1ccc(OCCCc2ccc(OCCCCOc3ccccc3)cc2)c(C=O)c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(OCCCCOc2ccc(CCCOc3ccccc3)cc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[C:5]-[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[c:7](:[c:9]):[c:6]-[C:5]=[O;D1;H0:4] | 80.9 | [{"value": 80.9, "product": "C(=O)C=1C=C(C(=O)OCC)C=CC1OCCCC1=CC=C(C=C1)OCCCCOC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 16 | HOUR | 1.37 g (3.76 mmol) of 1-(3-bromopropyl)-4-(4-phenoxybutoxy)benzene, 0.79 g (3.76 mmol) of ethyl 3-formyl-4-hydroxybenzoate [CAS No. 82304-99-2] and 0.78 g (5.64 mmol) of potassium carbonate are dissolved in 20 ml of DMF, and the mixture is stirred at 40° C. for 16 hours. It is then concentrated, and the residue is take... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HBr | CN(C)C=O | 40 | 16 | BrCCCc1ccc(OCCCCOc2ccccc2)cc1.CCOC(=O)c1ccc(O)c(C=O)c1>CN(C)C=O>CCOC(=O)c1ccc(OCCCc2ccc(OCCCCOc3ccccc3)cc2)c(C=O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c2f4024679f74012814baf3d66fc9ffb | BrCCCc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1.CCOC(=O)c1ccc(O)c(C=O)c1>>CCOC(=O)c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C=O)c1 | BrCCCC1=CC=C(C=C1)OCC1=CC=C(C=C1)C1=CC=CC=C1.C(=O)C=1C=C(C(=O)OCC)C=CC1O>>C1(=CC=C(C=C1)COC1=CC=C(C=C1)CCCOC1=C(C=C(C(=O)OCC)C=C1)C=O)C1=CC=CC=C1 | Br[CH2:11][CH2:12][CH2:13][c:14]1[cH:15][cH:16][c:17]([O:18][CH2:19][c:20]2[cH:21][cH:22][c:23](-[c:24]3[cH:25][cH:26][cH:27][cH:28][cH:29]3)[cH:30][cH:31]2)[cH:32][cH:33]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([OH:10])[c:34]([CH:35]=[O:36])[cH:37]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][... | BrCCCc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1.CCOC(=O)c1ccc(O)c(C=O)c1 | CCOC(=O)c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C=O)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[C:5]-[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[c:7](:[c:9]):[c:6]-[C:5]=[O;D1;H0:4] | null | [] | null | null | null | null | Preparation takes place in analogy to Example XIII from 1,1′-biphenyl-4-ylmethyl 4-(3-bromopropyl)phenyl ether and ethyl 3-formyl-4-hydroxybenzoate.
Conditions: See reaction.notes.procedure_details.
Workup: Preparation | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HBr | null | null | null | BrCCCc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1.CCOC(=O)c1ccc(O)c(C=O)c1>>CCOC(=O)c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C=O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-348c7664cc3549788635a54d1e6885a4 | CCOC(=O)c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C=O)c1.NS(=O)(=O)O>>CCOC(=O)c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)O)c1 | Cl(=O)[O-].[Na+].S(N)(O)(=O)=O.C1(=CC=C(C=C1)COC1=CC=C(C=C1)CCCOC1=C(C=C(C(=O)OCC)C=C1)C=O)C1=CC=CC=C1.C1CCOC1>>C1(=CC=C(C=C1)COC1=CC=C(C=C1)CCCOC1=C(C(=O)O)C=C(C=C1)C(=O)OCC)C1=CC=CC=C1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][c:17]([O:18][CH2:19][c:20]3[cH:21][cH:22][c:23](-[c:24]4[cH:25][cH:26][cH:27][cH:28][cH:29]4)[cH:30][cH:31]3)[cH:32][cH:33]2)[c:34]([CH:35]=[O:36])[cH:38]1.NS(=O)(=O)[OH:37]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]... | CCOC(=O)c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C=O)c1.NS(=O)(=O)O | CCOC(=O)c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)O)c1 | null | null | O | Acylation | OtherReaction | f287b39bba0c1b0397a4f00e499125db790c794585d77f89499d60ab3c26798d | a8ae608e736a38cb1830db0bc435afaf4aadee39cc7dd85eee29358304f341fb | c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)cc1 | N-S(=O)(=O)-[OH;D1;+0:1].[O;D1;H0:2]=[CH;D2;+0:3]-[c:4](:[c:5]):[c:6]>>[O;D1;H0:2]=[C;H0;D3;+0:3](-[OH;D1;+0:1])-[c:4](:[c:5]):[c:6] | null | [] | 0 | CELSIUS | 15 | MINUTE | 3.10 g (6.28 mmol) of ethyl 4-{3-[4-(1,1′-biphenyl-4-ylmethoxy)phenyl]propoxy}-3-formylbenzoate are introduced into 50 ml of THF. At about 0° C. (internal temperature), solutions of 2.13 g (18.8 nmol) of sodium chlorite in 2.5 ml of water and 1.83 g (18.8 mmol) of sulphamic acid in 9 ml of water are simultaneously adde... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Aldehyde | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | O | 0 | 0.25 | CCOC(=O)c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C=O)c1.NS(=O)(=O)O>O>CCOC(=O)c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-de5d8c77679b477e87e86417d7ec09d3 | BrCCCCBr.OCC1CC1>>BrCCCCOCC1CC1 | BrCCCCBr.[H-].[Na+].OCC1CC1.O>>BrCCCCOCC1CC1 | Br[CH2:5][CH2:4][CH2:3][CH2:2][Br:1].[OH:6][CH2:7][CH:8]1[CH2:9][CH2:10]1>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH2:7][CH:8]1[CH2:9][CH2:10]1 | BrCCCCBr.OCC1CC1 | BrCCCCOCC1CC1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | C1CC1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[C:5]-[C:4] | null | [] | 100 | CELSIUS | 15 | HOUR | 2.8 g of a 60% suspension of sodium hydride in mineral oil are added in portions to a solution of 5.0 g of hydroxymethylcyclopropane in 25 ml of toluene at room temperature. The mixture is then heated at 100° C. for 2 hours. After this, it is allowed to reach room temperature and a solution of 14.9 g of 1,4-dibromobuta... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | C1CC1 | HBr | C1(=CC=CC=C1)C | 100 | 15 | BrCCCCBr.OCC1CC1>C1(=CC=CC=C1)C>BrCCCCOCC1CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6fe965fc47684100a91102a5f2795b52 | CCOC(=O)C=Cc1ccc(C=O)cc1.c1ccc(OCCCC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>>CCOC(=O)/C=C/c1ccc(C=CCCCOc2ccccc2)cc1 | C(=O)C1=CC=C(C=CC(=O)OCC)C=C1.[Br-].O(C1=CC=CC=C1)CCCC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(CCC)[Li]>>O(C1=CC=CC=C1)CCCC=CC1=CC=C(C=C1)/C=C/C(=O)OCC | O=[CH:12][c:11]1[cH:10][cH:9][c:8]([CH:7]=[CH:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:25][cH:24]1.c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:13][CH2:14][CH2:15][CH2:16][O:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)cc1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])/[CH:6]=[CH:7]/[c:8]1[cH:9][cH:10][c:11]([CH:12]=[CH:13][CH2:14][CH2:15][C... | CCOC(=O)C=Cc1ccc(C=O)cc1.c1ccc(OCCCC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | CCOC(=O)/C=C/c1ccc(C=CCCCOc2ccccc2)cc1 | null | null | C1CCOC1 | C-C Coupling | Wittig with Phosphonium | cb5f277ac55a0e763ef643becc05f1522019cc4161daceb249ed2d634b78153b | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | C(=Cc1ccccc1)CCCOc1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[CH2;D2;+0:7]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:5]-[C:6]-[CH;D2;+0:7]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 65 | [{"value": 65.0, "product": "O(C1=CC=CC=C1)CCCC=CC1=CC=C(C=C1)/C=C/C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -40 | CELSIUS | null | null | 3.16 g of (4-phenoxybutyl)(triphenyl)phosphonium bromide are suspended in 25 ml of THF under argon and cooled to −40° C. 2.36 ml of n-butyllithium (1.6 molar in hexane) are added dropwise, and the mixture is warmed to 0° C. after 5 minutes and cooled again to −40° C. after 15 minutes. A solution of 0.70 g of ethyl 4-fo... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1.c1ccccc1 | HO- | C1CCOC1 | -40 | null | CCOC(=O)C=Cc1ccc(C=O)cc1.c1ccc(OCCCC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>C1CCOC1>CCOC(=O)/C=C/c1ccc(C=CCCCOc2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e4b7e31ae7d9410193a1d5c6e20b8ac8 | OC/C=C/c1ccc(C=CCCCOc2ccccc2)cc1>>OCCCc1ccc(CCCCCOc2ccccc2)cc1 | [H][H].O(C1=CC=CC=C1)CCCC=CC1=CC=C(C=C1)/C=C/CO>>O(C1=CC=CC=C1)CCCCCC1=CC=C(C=C1)CCCO | [OH:1][CH2:2]/[CH:3]=[CH:4]/[c:5]1[cH:6][cH:7][c:8]([CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][O:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21][cH:22]1>>[OH:1][CH2:2][CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21][cH:22]1 | OC/C=C/c1ccc(C=CCCCOc2ccccc2)cc1 | OCCCc1ccc(CCCCCOc2ccccc2)cc1 | null | [Pd] | C(C)(=O)OCC | Reduction | OtherReaction | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccc(CCCCCOc2ccccc2)cc1 | [C:1]-[C:2]-[CH;D2;+0:3]=[CH;D2;+0:4]-[c:5]1:[c:6]:[c:7]:[c:8](/[CH;D2;+0:9]=[CH;D2;+0:10]/[C:11]-[O;D1;H1:12]):[c:13]:[c:14]:1>>[C:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[c:5]1:[c:6]:[c:7]:[c:8](-[CH2;D2;+0:9]-[CH2;D2;+0:10]-[C:11]-[O;D1;H1:12]):[c:13]:[c:14]:1 | 53.4 | [{"value": 53.4, "product": "O(C1=CC=CC=C1)CCCCCC1=CC=C(C=C1)CCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | About 5 mg of palladium on carbon (10%) are added to a solution of 98 mg of (2E)-3-{4-[5-phenoxypent-1-en-1-yl]phenyl}prop-2-en-1-ol in about 5 ml of ethyl acetate, and the mixture is hydrogenated under 1 bar of hydrogen at room temperature overnight. The mixture is filtered to remove catalyst and concentrated, and the... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccccc1 | null | [Pd].C(C)(=O)OCC | null | null | OC/C=C/c1ccc(C=CCCCOc2ccccc2)cc1>[Pd].C(C)(=O)OCC>OCCCc1ccc(CCCCCOc2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c2050ca9395a42369f1b9ec3d13eccee | BrCc1ccc(-c2ccccc2)cc1.CC(=O)Oc1ccc(O)cc1>>CC(=O)Oc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1 | C([O-])([O-])=O.[K+].[K+].C1=CC=C(C=C1)C2=CC=C(C=C2)CBr.C(C)(=O)OC1=CC=C(C=C1)O>>C(C)(=O)OC1=CC=C(C=C1)OCC1=CC=C(C=C1)C1=CC=CC=C1 | Br[CH2:10][c:11]1[cH:12][cH:13][c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21][cH:22]1.[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:23][cH:24]1>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:21][cH:22... | BrCc1ccc(-c2ccccc2)cc1.CC(=O)Oc1ccc(O)cc1 | CC(=O)Oc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1 | null | null | C(CCC)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(OCc2ccc(-c3ccccc3)cc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | 37.8 | [{"value": 37.8, "product": "C(C)(=O)OC1=CC=C(C=C1)OCC1=CC=C(C=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 8 | HOUR | 2.35 g of anhydrous potassium carbonate are added to a solution of 2.80 g of 4-biphenylmethyl bromide and 1.72 g of 4-hydroxyphenyl acetate in 75 ml of butyronitrile, and the reaction mixture is stirred at 120° C. overnight. It is filtered with suction, washed with acetonitrile, and concentrated. The residue is taken u... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HBr | C(CCC)#N | 120 | 8 | BrCc1ccc(-c2ccccc2)cc1.CC(=O)Oc1ccc(O)cc1>C(CCC)#N>CC(=O)Oc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a1467a0cad4b4895b545d78df6710d60 | BrC(Br)(Br)Br.OCCOc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1>>BrCCOc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1 | C1(=CC=C(C=C1)COC1=CC=C(OCCO)C=C1)C1=CC=CC=C1.BrC(Br)(Br)Br.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>BrCCOC1=CC=C(OCC2=CC=C(C=C2)C2=CC=CC=C2)C=C1 | BrC(Br)(Br)[Br:1].O[CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:21][cH:22]2)[cH:23][cH:24]1>>[Br:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:... | BrC(Br)(Br)Br.OCCOc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1 | BrCCOc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1 | null | null | ClCCl | Functional Group Interconversion | Appel reaction | 752e1807cd47d8316010cc3f92eab16c5a89ffb844d9514fcae469ba993c78dd | 2c6b51fb1e17cb2c93d565e0423c75825df2c8e11c870e0c98b278f20ba9f3ad | c1ccc(OCc2ccc(-c3ccccc3)cc2)cc1 | Br-C(-Br)(-Br)-[Br;H0;D1;+0:1].O-[CH2;D2;+0:2]-[C:3]-[#8:4]>>[#8:4]-[C:3]-[CH2;D2;+0:2]-[Br;H0;D1;+0:1] | 50.2 | [{"value": 50.2, "product": "BrCCOC1=CC=C(OCC2=CC=C(C=C2)C2=CC=CC=C2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 10 | MINUTE | 800 mg of 2-[4-(biphenyl-4-ylmethoxy)phenoxy]ethanol are introduced into 25 ml of dichloromethane under argon, 1.16 g of tetrabromomethane are added, and the mixture is stirred at room temperture for 10 minutes. The mixture is cooled to 0° C. and, after addition of 1.83 g of triphenylphosphine, stirred at 0° C. for one... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Primary alcohol | Primary halide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HBr | ClCCl | 0 | 0.166667 | BrC(Br)(Br)Br.OCCOc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1>ClCCl>BrCCOc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-57a9bee3d10b4c43bc78f3b8c7e589e0 | COC(=O)COc1ccc(C=O)cc1.c1ccc(OCCCC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>>COC(=O)COc1ccc(C=CCCCOc2ccccc2)cc1 | C(=O)C1=CC=C(OCC(=O)OC)C=C1.[Br-].O(C1=CC=CC=C1)CCCC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>O(C1=CC=CC=C1)CCCC=CC1=CC=C(OCC(=O)OC)C=C1 | O=[CH:11][c:10]1[cH:9][cH:8][c:7]([O:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[cH:24][cH:23]1.c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:12][CH2:13][CH2:14][CH2:15][O:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)cc1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([CH:11]=[CH:12][CH2:13][CH2:14][CH2:15][O:16][c:17]2[... | COC(=O)COc1ccc(C=O)cc1.c1ccc(OCCCC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | COC(=O)COc1ccc(C=CCCCOc2ccccc2)cc1 | null | null | null | C-C Coupling | Wittig with Phosphonium | cb5f277ac55a0e763ef643becc05f1522019cc4161daceb249ed2d634b78153b | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | C(=Cc1ccccc1)CCCOc1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[CH2;D2;+0:7]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:5]-[C:6]-[CH;D2;+0:7]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | Preparation takes place in analogy to Example XLIII from methyl (4-formylphenoxy)acetate and (4-phenoxybutyl)(triphenyl)phosphonium bromide. The product is obtained as an E/Z mixture.
Conditions: See reaction.notes.procedure_details.
Workup: Preparation; The product is obtained as an E/Z mixture | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | COC(=O)COc1ccc(C=O)cc1.c1ccc(OCCCC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>>COC(=O)COc1ccc(C=CCCCOc2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3e4bfe46485b49fd89617f5462f96148 | CCOC(=O)CCc1ccc(C=O)cc1.c1ccc(OCCCC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>>CCOC(=O)CCc1ccc(C=CCCCOc2ccccc2)cc1 | [Br-].O(C1=CC=CC=C1)CCCC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(=O)C1=CC=C(C=C1)CCC(=O)OCC>>O(C1=CC=CC=C1)CCCC=CC1=CC=C(C=C1)CCC(=O)OCC | O=[CH:12][c:11]1[cH:10][cH:9][c:8]([CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:25][cH:24]1.c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:13][CH2:14][CH2:15][CH2:16][O:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)cc1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]([CH:12]=[CH:13][CH2:14][CH2:15][C... | CCOC(=O)CCc1ccc(C=O)cc1.c1ccc(OCCCC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | CCOC(=O)CCc1ccc(C=CCCCOc2ccccc2)cc1 | null | null | null | C-C Coupling | Wittig with Phosphonium | cb5f277ac55a0e763ef643becc05f1522019cc4161daceb249ed2d634b78153b | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | C(=Cc1ccccc1)CCCOc1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[CH2;D2;+0:7]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:5]-[C:6]-[CH;D2;+0:7]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | Preparation takes place in analogy to Example XLIII from (4-phenoxybutyl)-(triphenyl)phosphonium bromide and ethyl 3-(4-formylphenyl)propanoate. The product is obtained as an E/Z mixture.
Conditions: See reaction.notes.procedure_details.
Workup: Preparation; The product is obtained as an E/Z mixture | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1.c1ccccc1 | HO- | null | null | null | CCOC(=O)CCc1ccc(C=O)cc1.c1ccc(OCCCC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>>CCOC(=O)CCc1ccc(C=CCCCOc2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4c0ada2053124579aa7f52ab98dd5765 | CC(C)[Si](Oc1ccc(CCCBr)cc1)(C(C)C)C(C)C.COC(=O)c1ccc(O)c(C(=O)N2CCC(C(=O)OC)CC2)c1>>COC(=O)c1ccc(OCCCc2ccc(O[Si](C(C)C)(C(C)C)C(C)C)cc2)c(C(=O)N2CCC(C(=O)OC)CC2)c1 | BrCCCC1=CC=C(O[Si](C(C)C)(C(C)C)C(C)C)C=C1.OC1=C(C(=O)N2CCC(CC2)C(=O)OC)C=C(C=C1)C(=O)OC>>COC(=O)C=1C=CC(=C(C(=O)N2CCC(CC2)C(=O)OC)C1)OCCCC1=CC=C(C=C1)O[Si](C(C)C)(C(C)C)C(C)C | Br[CH2:10][CH2:11][CH2:12][c:13]1[cH:14][cH:15][c:16]([O:17][Si:18]([CH:19]([CH3:20])[CH3:21])([CH:22]([CH3:23])[CH3:24])[CH:25]([CH3:26])[CH3:27])[cH:28][cH:29]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:30]([C:31](=[O:32])[N:33]2[CH2:34][CH2:35][CH:36]([C:37](=[O:38])[O:39][CH3:40])[CH2:41][CH2:42]2)... | CC(C)[Si](Oc1ccc(CCCBr)cc1)(C(C)C)C(C)C.COC(=O)c1ccc(O)c(C(=O)N2CCC(C(=O)OC)CC2)c1 | COC(=O)c1ccc(OCCCc2ccc(O[Si](C(C)C)(C(C)C)C(C)C)cc2)c(C(=O)N2CCC(C(=O)OC)CC2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(c1ccccc1OCCCc1ccccc1)N1CCCCC1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[#7:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:10] | null | [] | null | null | null | null | Methyl 1-[5-(methoxycarbonyl)-2-(3-{4-[(triisopropylsilyl)oxy]phenyl}propoxy)-benzoyl]piperidine-4-carboxylate is prepared by the process described in Example XLI from [4-(3-bromopropyl)phenoxy](triisopropyl)silane and methyl 1-[2-hydroxy-5-(methoxycarbonyl)benzoyl]-4-piperidinecarboxylate.
Conditions: See reaction.not... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.C1CC[NH]CC1 | HBr | null | null | null | CC(C)[Si](Oc1ccc(CCCBr)cc1)(C(C)C)C(C)C.COC(=O)c1ccc(O)c(C(=O)N2CCC(C(=O)OC)CC2)c1>>COC(=O)c1ccc(OCCCc2ccc(O[Si](C(C)C)(C(C)C)C(C)C)cc2)c(C(=O)N2CCC(C(=O)OC)CC2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b84c59f2dcf04e7f80bc6f293a54a439 | BrCCCc1ccc(OCCCCOc2ccccc2)cc1.COC(=O)c1ccc(O)c(C(=O)N2CCC(C(=O)OC)CC2)c1>>COC(=O)c1ccc(OCCCc2ccc(OCCCCOc3ccccc3)cc2)c(C(=O)N2CCC(C(=O)OC)CC2)c1 | BrCCCC1=CC=C(C=C1)OCCCCOC1=CC=CC=C1.OC1=C(C(=O)N2CCC(CC2)C(=O)OC)C=C(C=C1)C(=O)OC>>COC(=O)C=1C=CC(=C(C(=O)N2CCC(CC2)C(=O)OC)C1)OCCCC1=CC=C(C=C1)OCCCCOC1=CC=CC=C1 | Br[CH2:10][CH2:11][CH2:12][c:13]1[cH:14][cH:15][c:16]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[cH:29][cH:30]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:31]([C:32](=[O:33])[N:34]2[CH2:35][CH2:36][CH:37]([C:38](=[O:39])[O:40][CH3:41])[CH2:42][CH2:43]2)[cH:4... | BrCCCc1ccc(OCCCCOc2ccccc2)cc1.COC(=O)c1ccc(O)c(C(=O)N2CCC(C(=O)OC)CC2)c1 | COC(=O)c1ccc(OCCCc2ccc(OCCCCOc3ccccc3)cc2)c(C(=O)N2CCC(C(=O)OC)CC2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(c1ccccc1OCCCc1ccc(OCCCCOc2ccccc2)cc1)N1CCCCC1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[#7:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:10] | null | [] | null | null | null | null | Methyl 1-(5-(methoxycarbonyl)-2-{3-[4-(4-phenoxybutoxy)phenyl]propoxy}-benzoyl)-4-piperidinecarboxylate is prepared in analogy to the process described in Example 2 from 1-(3-bromopropyl)-4-(4-phenoxybutoxy)benzene and methyl 1-[2-hydroxy-5-(methoxycarbonyl)benzoyl]-4-piperidinecarboxylate.
Conditions: See reaction.not... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CC[NH]CC1 | HBr | null | null | null | BrCCCc1ccc(OCCCCOc2ccccc2)cc1.COC(=O)c1ccc(O)c(C(=O)N2CCC(C(=O)OC)CC2)c1>>COC(=O)c1ccc(OCCCc2ccc(OCCCCOc3ccccc3)cc2)c(C(=O)N2CCC(C(=O)OC)CC2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d2b43d784765443f96e992ce4337d8c8 | CCOC(=O)c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)O)c1.COC(=O)C1CCNCC1>>CCOC(=O)c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)N2CCC(C(=O)OC)CC2)c1 | O.ON1N=NC2=C1C=CC=C2.C(C)N(CC)CC.C1(=CC=C(C=C1)COC1=CC=C(C=C1)CCCOC1=C(C(=O)O)C=C(C=C1)C(=O)OCC)C1=CC=CC=C1.Cl.N1CCC(CC1)C(=O)OC>>C1(=CC=C(C=C1)COC1=CC=C(C=C1)CCCOC1=C(C(=O)N2CCC(CC2)C(=O)OC)C=C(C=C1)C(=O)OCC)C1=CC=CC=C1 | O[C:35]([c:34]1[c:9]([O:10][CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][c:17]([O:18][CH2:19][c:20]3[cH:21][cH:22][c:23](-[c:24]4[cH:25][cH:26][cH:27][cH:28][cH:29]4)[cH:30][cH:31]3)[cH:32][cH:33]2)[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:47]1)=[O:36].[NH:37]1[CH2:38][CH2:39][CH:40]([C:41](=[O:42])[O:43][... | CCOC(=O)c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)O)c1.COC(=O)C1CCNCC1 | CCOC(=O)c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)N2CCC(C(=O)OC)CC2)c1 | null | null | ClCCl.O | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | fbfce93ec1ece674255bb96c5cec09ad611382b41cf117dfe580015e21744a71 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1ccccc1OCCCc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1)N1CCCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:9]-[C:10] | 96.4 | [{"value": 96.4, "product": "C1(=CC=C(C=C1)COC1=CC=C(C=C1)CCCOC1=C(C(=O)N2CCC(CC2)C(=O)OC)C=C(C=C1)C(=O)OCC)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 75 mg of N-[(3-dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (EDC), 27 mg of 1-hydroxy-1H-benzotriazole hydrate (HOBT) and 40 mg of triethylamine, are successively added to a suspension of 100 mg of 2-{3-[4-(1,1′-biphenyl-4-ylmethoxy)phenyl]propoxy}-5-(ethoxycarbonyl)benzoic acid and 39 mg of methyl piperidi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.C1CC[NH]CC1 | HO- | ClCCl.O | null | null | CCOC(=O)c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)O)c1.COC(=O)C1CCNCC1>ClCCl.O>CCOC(=O)c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)N2CCC(C(=O)OC)CC2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-77fa3758660f4895aa3a3902960c4cca | CCOC(=O)[C@@H]1CCCC[C@@H]1N.CCOC(=O)c1ccc(OCCCc2ccc(OCCCCOc3ccccc3)cc2)c(C(=O)O)c1>>CCOC(=O)c1ccc(OCCCc2ccc(OCCCCOc3ccccc3)cc2)c(C(=O)N[C@@H]2CCCC[C@@H]2C(=O)OCC)c1 | O.ON1N=NC2=C1C=CC=C2.C(C)OC(=O)C=1C=CC(=C(C(=O)O)C1)OCCCC1=CC=C(C=C1)OCCCCOC1=CC=CC=C1.C(C)N(CC)CC.Cl.N[C@@H]1[C@@H](CCCC1)C(=O)OCC>>C(C)OC(=O)[C@@H]1[C@@H](CCCC1)NC(=O)C=1C=C(C(=O)OCC)C=CC1OCCCC1=CC=C(C=C1)OCCCCOC1=CC=CC=C1 | [NH2:35][C@H:36]1[CH2:37][CH2:38][CH2:39][CH2:40][C@H:41]1[C:42](=[O:43])[O:44][CH2:45][CH3:46].O[C:33]([c:32]1[c:9]([O:10][CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][c:17]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][c:24]3[cH:25][cH:26][cH:27][cH:28][cH:29]3)[cH:30][cH:31]2)[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:... | CCOC(=O)[C@@H]1CCCC[C@@H]1N.CCOC(=O)c1ccc(OCCCc2ccc(OCCCCOc3ccccc3)cc2)c(C(=O)O)c1 | CCOC(=O)c1ccc(OCCCc2ccc(OCCCCOc3ccccc3)cc2)c(C(=O)N[C@@H]2CCCC[C@@H]2C(=O)OCC)c1 | null | null | ClCCl.O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NC1CCCCC1)c1ccccc1OCCCc1ccc(OCCCCOc2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#8:6]-[C:7](=[O;D1;H0:8])-[C:9]-[C:10](-[NH2;D1;+0:11])-[C:12]>>[#8:6]-[C:7](=[O;D1;H0:8])-[C:9]-[C:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:12] | 87.7 | [{"value": 87.7, "product": "C(C)OC(=O)[C@@H]1[C@@H](CCCC1)NC(=O)C=1C=C(C(=O)OCC)C=CC1OCCCC1=CC=C(C=C1)OCCCCOC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 39 mg (0.20 mmol) of N-[(3-dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (EDC) and 27.4 mg (0.20 mmol) of 1-hydroxy-1H-benzotriazole hydrate (HOBT) are successively added to a suspension of 100 mg (0.20 mmol) of 5-(ethoxycarbonyl)-2-{3-[4-(4-phenoxybutoxy)phenyl]propoxy}benzoic acid in 30 ml of dichlorometha... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CCCCC1 | HO- | ClCCl.O | null | 0.5 | CCOC(=O)[C@@H]1CCCC[C@@H]1N.CCOC(=O)c1ccc(OCCCc2ccc(OCCCCOc3ccccc3)cc2)c(C(=O)O)c1>ClCCl.O>CCOC(=O)c1ccc(OCCCc2ccc(OCCCCOc3ccccc3)cc2)c(C(=O)N[C@@H]2CCCC[C@@H]2C(=O)OCC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7466348edf73467aa2ea84e6b996d0dc | CCOC(=O)c1ccc(OCCCc2ccc(OCCCCOc3ccccc3)cc2)c(C(=O)O)c1.COC(=O)C1CNC1>>CCOC(=O)c1ccc(OCCCc2ccc(OCCCCOc3ccccc3)cc2)c(C(=O)N2CC(C(=O)OC)C2)c1 | C(C)OC(=O)C=1C=CC(=C(C(=O)O)C1)OCCCC1=CC=C(C=C1)OCCCCOC1=CC=CC=C1.N1CC(C1)C(=O)OC>>C(C)OC(=O)C=1C=CC(=C(C(=O)N2CC(C2)C(=O)OC)C1)OCCCC1=CC=C(C=C1)OCCCCOC1=CC=CC=C1 | O[C:33]([c:32]1[c:9]([O:10][CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][c:17]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][c:24]3[cH:25][cH:26][cH:27][cH:28][cH:29]3)[cH:30][cH:31]2)[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:43]1)=[O:34].[NH:35]1[CH2:36][CH:37]([C:38](=[O:39])[O:40][CH3:41])[CH2:42]1>>[CH3... | CCOC(=O)c1ccc(OCCCc2ccc(OCCCCOc3ccccc3)cc2)c(C(=O)O)c1.COC(=O)C1CNC1 | CCOC(=O)c1ccc(OCCCc2ccc(OCCCCOc3ccccc3)cc2)c(C(=O)N2CC(C(=O)OC)C2)c1 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac1482ab6697c5dd73a4882e2d504ff2937dd92d151bbb05c4c4f2d3fc052f5d | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1ccccc1OCCCc1ccc(OCCCCOc2ccccc2)cc1)N1CCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#8:6]-[C:7](=[O;D1;H0:8])-[C:9]1-[C:10]-[NH;D2;+0:11]-[C:12]-1>>[#8:6]-[C:7](=[O;D1;H0:8])-[C:9]1-[C:10]-[N;H0;D3;+0:11](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:12]-1 | null | [] | null | null | null | null | The compound is prepared in analogy to the process described in Example 6 from 5-(ethoxycarbonyl)-2-{3-[4-(4-phenoxybutoxy)phenyl]propoxy}benzoic acid and methyl 3-azetidinecarboxylate [CAS No. 343238-58-4]. The crude product is immediately reacted further without purification.
Conditions: See reaction.notes.procedure_... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CNC1 | C1C[NH]C1 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH]C1 | HO- | null | null | null | CCOC(=O)c1ccc(OCCCc2ccc(OCCCCOc3ccccc3)cc2)c(C(=O)O)c1.COC(=O)C1CNC1>>CCOC(=O)c1ccc(OCCCc2ccc(OCCCCOc3ccccc3)cc2)c(C(=O)N2CC(C(=O)OC)C2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-969d106c55664a6ea8e261b2cbb9ca78 | CCOC(=O)[C@@H]1CCCC[C@@H]1N.CCOC(=O)c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)O)c1>>CCOC(=O)c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)N[C@@H]2CCCC[C@@H]2C(=O)OCC)c1 | C1(=CC=C(C=C1)COC1=CC=C(C=C1)CCCOC1=C(C(=O)O)C=C(C=C1)C(=O)OCC)C1=CC=CC=C1.Cl.N[C@@H]1[C@@H](CCCC1)C(=O)OCC>>C1(=CC=C(C=C1)COC1=CC=C(C=C1)CCCOC1=C(C=C(C(=O)OCC)C=C1)C(=O)N[C@H]1[C@H](CCCC1)C(=O)OCC)C1=CC=CC=C1 | [NH2:37][C@H:38]1[CH2:39][CH2:40][CH2:41][CH2:42][C@H:43]1[C:44](=[O:45])[O:46][CH2:47][CH3:48].O[C:35]([c:34]1[c:9]([O:10][CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][c:17]([O:18][CH2:19][c:20]3[cH:21][cH:22][c:23](-[c:24]4[cH:25][cH:26][cH:27][cH:28][cH:29]4)[cH:30][cH:31]3)[cH:32][cH:33]2)[cH:8][cH:7][c:6]([C:4]([O... | CCOC(=O)[C@@H]1CCCC[C@@H]1N.CCOC(=O)c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)O)c1 | CCOC(=O)c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)N[C@@H]2CCCC[C@@H]2C(=O)OCC)c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NC1CCCCC1)c1ccccc1OCCCc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#8:6]-[C:7](=[O;D1;H0:8])-[C:9]-[C:10](-[NH2;D1;+0:11])-[C:12]>>[#8:6]-[C:7](=[O;D1;H0:8])-[C:9]-[C:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:12] | null | [] | null | null | null | null | The compound is prepared in analogy to the process described in Example 6 from 2-{3-[4-(1,1′-biphenyl-4-ylmethoxy)phenyl]propoxy}-5-(ethoxycarbonyl)benzoic acid and ethyl cis-2-amino-1-cyclohexanecarboxylate hydrochloride.
Conditions: See reaction.notes.procedure_details.
Workup: The compound is prepared in analogy to ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.C1CCCCC1 | HO- | null | null | null | CCOC(=O)[C@@H]1CCCC[C@@H]1N.CCOC(=O)c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)O)c1>>CCOC(=O)c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)N[C@@H]2CCCC[C@@H]2C(=O)OCC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-14a7fad44c494ab0905b28a98cfe47e0 | COC(=O)c1ccc(OCCCc2ccc(OCCCCOc3ccccc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1>>O=C(O)c1ccc(OCCCc2ccc(OCCCCOc3ccccc3)cc2)c(C(=O)NC2CCCC(C(=O)O)C2)c1 | COC(=O)C1CC(CCC1)NC(=O)C=1C=C(C(=O)OC)C=CC1OCCCC1=CC=C(C=C1)OCCCCOC1=CC=CC=C1.[OH-].[Na+].Cl>>C(=O)(O)C1CC(CCC1)NC(=O)C=1C=C(C(=O)O)C=CC1OCCCC1=CC=C(C=C1)OCCCCOC1=CC=CC=C1 | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][CH2:10][CH2:11][c:12]2[cH:13][cH:14][c:15]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][c:22]3[cH:23][cH:24][cH:25][cH:26][cH:27]3)[cH:28][cH:29]2)[c:30]([C:31](=[O:32])[NH:33][CH:34]2[CH2:35][CH2:36][CH2:37][CH:38]([C:39](=[O:40])[O:41]C)[CH2:42]2)[cH:43]1>>[O:1]... | COC(=O)c1ccc(OCCCc2ccc(OCCCCOc3ccccc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | O=C(O)c1ccc(OCCCc2ccc(OCCCCOc3ccccc3)cc2)c(C(=O)NC2CCCC(C(=O)O)C2)c1 | null | null | O1CCCC1.CO | Deprotection | OtherReaction | 6e62db7aac546f574bcfb83067ba8906c30fcbfedfc37aa16b5eaad33833f45a | ed5fed81ba501ef41c88831ec6b9463b899bfdd0815c4145ae51c79addb226d0 | O=C(NC1CCCCC1)c1ccccc1OCCCc1ccc(OCCCCOc2ccccc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].C-[O;H0;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[O;D1;H0:7]=[C:6](-[OH;D1;+0:5])-[c:8] | 96.7 | [{"value": 96.7, "product": "C(=O)(O)C1CC(CCC1)NC(=O)C=1C=C(C(=O)O)C=CC1OCCCC1=CC=C(C=C1)OCCCCOC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | A solution of 638 mg of methyl 3-({[3-(methoxycarbonyl)cyclohexyl]-amino}carbonyl)-4-{3-[4-(4-phenoxybutoxy)phenyl]propoxy}benzoate (racemate B) in 4 ml of tetrahydrofuran (THF) and 4 ml of methanol is mixed with 4 ml of 2 molar sodium hydroxide solution and heated at 60° C. for one hour. The pH is then adjusted to a v... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CCCCC1 | Other | O1CCCC1.CO | 60 | null | COC(=O)c1ccc(OCCCc2ccc(OCCCCOc3ccccc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1>O1CCCC1.CO>O=C(O)c1ccc(OCCCc2ccc(OCCCCOc3ccccc3)cc2)c(C(=O)NC2CCCC(C(=O)O)C2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1ae4e980a4fb459295f4e4e2bc944e54 | COC(=O)c1ccc(OCCCc2ccc(OCCCC3CCCCC3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1>>O=C(O)c1ccc(OCCCc2ccc(OCCCC3CCCCC3)cc2)c(C(=O)NC2CCCC(C(=O)O)C2)c1 | C1(CCCCC1)CCCOC1=CC=C(C=C1)CCCOC1=C(C=C(C(=O)OC)C=C1)C(=O)NC1CC(CCC1)C(=O)OC.[OH-].[Na+]>>C(=O)(O)C1CC(CCC1)NC(=O)C=1C=C(C(=O)O)C=CC1OCCCC1=CC=C(C=C1)OCCCC1CCCCC1 | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][CH2:10][CH2:11][c:12]2[cH:13][cH:14][c:15]([O:16][CH2:17][CH2:18][CH2:19][CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]3)[cH:26][cH:27]2)[c:28]([C:29](=[O:30])[NH:31][CH:32]2[CH2:33][CH2:34][CH2:35][CH:36]([C:37](=[O:38])[O:39]C)[CH2:40]2)[cH:41]1>>[O:1]=[C:2]([... | COC(=O)c1ccc(OCCCc2ccc(OCCCC3CCCCC3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | O=C(O)c1ccc(OCCCc2ccc(OCCCC3CCCCC3)cc2)c(C(=O)NC2CCCC(C(=O)O)C2)c1 | null | null | CO.C1CCOC1 | Deprotection | OtherReaction | 6e62db7aac546f574bcfb83067ba8906c30fcbfedfc37aa16b5eaad33833f45a | ed5fed81ba501ef41c88831ec6b9463b899bfdd0815c4145ae51c79addb226d0 | O=C(NC1CCCCC1)c1ccccc1OCCCc1ccc(OCCCC2CCCCC2)cc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].C-[O;H0;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[O;D1;H0:7]=[C:6](-[OH;D1;+0:5])-[c:8] | 89.7 | [{"value": 89.7, "product": "C(=O)(O)C1CC(CCC1)NC(=O)C=1C=C(C(=O)O)C=CC1OCCCC1=CC=C(C=C1)OCCCC1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 1 | HOUR | A solution of 90.73 g of methyl 4-{3-[4-(3-cyclohexylpropoxy)phenyl]propoxy}-3-({[3-(methoxycarbonyl)cyclohexyl]amino}carbonyl)benzoate in 500 ml of THF and 500 ml of methanol is mixed with 300 ml of 2 molar sodium hydroxide solution and heated to 60° C. After one hour, the organic solvents are removed as far as possib... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1.c1ccccc1.C1CCCCC1.C1CCCCC1 | Other | CO.C1CCOC1 | 60 | 1 | COC(=O)c1ccc(OCCCc2ccc(OCCCC3CCCCC3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1>CO.C1CCOC1>O=C(O)c1ccc(OCCCc2ccc(OCCCC3CCCCC3)cc2)c(C(=O)NC2CCCC(C(=O)O)C2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5fedf11f68214768abfdd9f513edcbe2 | CCOC(=O)c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)O)c1.COC(=O)[C@@H]1CC[C@H](N)C1>>CCOC(=O)c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)N[C@H]2CC[C@@H](C(=O)OC)C2)c1 | C1(=CC=C(C=C1)COC1=CC=C(C=C1)CCCOC1=C(C(=O)O)C=C(C=C1)C(=O)OCC)C1=CC=CC=C1.Cl.N[C@@H]1C[C@@H](CC1)C(=O)OC>>C1(=CC=C(C=C1)COC1=CC=C(C=C1)CCCOC1=C(C=C(C(=O)OCC)C=C1)C(=O)N[C@@H]1C[C@@H](CC1)C(=O)OC)C1=CC=CC=C1 | O[C:35]([c:34]1[c:9]([O:10][CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][c:17]([O:18][CH2:19][c:20]3[cH:21][cH:22][c:23](-[c:24]4[cH:25][cH:26][cH:27][cH:28][cH:29]4)[cH:30][cH:31]3)[cH:32][cH:33]2)[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:47]1)=[O:36].[NH2:37][C@H:38]1[CH2:39][CH2:40][C@@H:41]([C:42](=[O:... | CCOC(=O)c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)O)c1.COC(=O)[C@@H]1CC[C@H](N)C1 | CCOC(=O)c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)N[C@H]2CC[C@@H](C(=O)OC)C2)c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NC1CCCC1)c1ccccc1OCCCc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7](-[NH2;D1;+0:8])-[C:9]>>[C:6]-[C:7](-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:9] | null | [] | null | null | null | null | Preparation takes place in analogy to Example 5 from 2-{3-[4-(1,1′-biphenyl-4-yl-methoxy)phenyl]propoxy}-5-(ethoxycarbonyl)benzoic acid and methyl (1R,3S)-3-aminocyclopentanecarboxylate hydrochloride.
Conditions: See reaction.notes.procedure_details.
Workup: Preparation | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.C1CCCC1 | HO- | null | null | null | CCOC(=O)c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)O)c1.COC(=O)[C@@H]1CC[C@H](N)C1>>CCOC(=O)c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)N[C@H]2CC[C@@H](C(=O)OC)C2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2aa9e34625c8478d9224be26a4d12629 | COC(=O)c1ccc(OCCCc2ccc(OCCCC3CCCCC3)cc2)c(C(=O)N2CCC(C(=O)OC)CC2)c1>>O=C(O)c1ccc(OCCCc2ccc(OCCCC3CCCCC3)cc2)c(C(=O)N2CCC(C(=O)O)CC2)c1 | C1(CCCCC1)CCCOC1=CC=C(C=C1)CCCOC1=C(C(=O)N2CCC(CC2)C(=O)OC)C=C(C=C1)C(=O)OC.[OH-].[Na+]>>C(=O)(O)C=1C=CC(=C(C(=O)N2CCC(CC2)C(=O)O)C1)OCCCC1=CC=C(C=C1)OCCCC1CCCCC1 | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][CH2:10][CH2:11][c:12]2[cH:13][cH:14][c:15]([O:16][CH2:17][CH2:18][CH2:19][CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]3)[cH:26][cH:27]2)[c:28]([C:29](=[O:30])[N:31]2[CH2:32][CH2:33][CH:34]([C:35](=[O:36])[O:37]C)[CH2:38][CH2:39]2)[cH:40]1>>[O:1]=[C:2]([OH:3])[c... | COC(=O)c1ccc(OCCCc2ccc(OCCCC3CCCCC3)cc2)c(C(=O)N2CCC(C(=O)OC)CC2)c1 | O=C(O)c1ccc(OCCCc2ccc(OCCCC3CCCCC3)cc2)c(C(=O)N2CCC(C(=O)O)CC2)c1 | null | null | CO.C1CCOC1 | Deprotection | OtherReaction | 6e62db7aac546f574bcfb83067ba8906c30fcbfedfc37aa16b5eaad33833f45a | ed5fed81ba501ef41c88831ec6b9463b899bfdd0815c4145ae51c79addb226d0 | O=C(c1ccccc1OCCCc1ccc(OCCCC2CCCCC2)cc1)N1CCCCC1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].C-[O;H0;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[O;D1;H0:7]=[C:6](-[OH;D1;+0:5])-[c:8] | 87.9 | [{"value": 87.9, "product": "C(=O)(O)C=1C=CC(=C(C(=O)N2CCC(CC2)C(=O)O)C1)OCCCC1=CC=C(C=C1)OCCCC1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 1 | HOUR | Absolution of 10.4 g of methyl 1-[2-{3-[4-(3-cyclohexylpropoxy)phenyl]propoxy}-5-(methoxycarbonyl)benzoyl]piperidine-4-carboxylate in a mixture of 160 ml of THF and 160 ml of methanol is mixed with 160 ml of 2 molar sodium hydroxide solution and stirred at a temperature of 60° C. for 1 hour. The organic solvents are th... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1.c1ccccc1.C1CCCCC1.C1CC[NH]CC1 | Other | CO.C1CCOC1 | 60 | 1 | COC(=O)c1ccc(OCCCc2ccc(OCCCC3CCCCC3)cc2)c(C(=O)N2CCC(C(=O)OC)CC2)c1>CO.C1CCOC1>O=C(O)c1ccc(OCCCc2ccc(OCCCC3CCCCC3)cc2)c(C(=O)N2CCC(C(=O)O)CC2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-99804e3a40f3441b94044a379b018da5 | COC(=O)c1ccc(OCCCc2ccc(OCCCC3OCC(C)(C)CO3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1>>COC(=O)c1ccc(OCCCc2ccc(OCCCC3OCC(C)(C)CO3)cc2)c(C(=O)NC2CCCC(C(=O)O)C2)c1 | CC1(COC(OC1)CCCOC1=CC=C(C=C1)CCCOC1=C(C=C(C(=O)OC)C=C1)C(=O)NC1CC(CCC1)C(=O)OC)C.Cl>>C(=O)(O)C1CC(CCC1)NC(=O)C=1C=C(C(=O)OC)C=CC1OCCCC1=CC=C(C=C1)OCCCC1OCC(CO1)(C)C | C[O:42][C:40]([CH:39]1[CH2:38][CH2:37][CH2:36][CH:35]([NH:34][C:32]([c:31]2[c:8]([O:9][CH2:10][CH2:11][CH2:12][c:13]3[cH:14][cH:15][c:16]([O:17][CH2:18][CH2:19][CH2:20][CH:21]4[O:22][CH2:23][C:24]([CH3:25])([CH3:26])[CH2:27][O:28]4)[cH:29][cH:30]3)[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:44]2)=[O:33])[CH2:43]1)=... | COC(=O)c1ccc(OCCCc2ccc(OCCCC3OCC(C)(C)CO3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | COC(=O)c1ccc(OCCCc2ccc(OCCCC3OCC(C)(C)CO3)cc2)c(C(=O)NC2CCCC(C(=O)O)C2)c1 | null | null | CO.[OH-].[Na+].C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(NC1CCCCC1)c1ccccc1OCCCc1ccc(OCCCC2OCCCO2)cc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 77.9 | [{"value": 77.9, "product": "C(=O)(O)C1CC(CCC1)NC(=O)C=1C=C(C(=O)OC)C=CC1OCCCC1=CC=C(C=C1)OCCCC1OCC(CO1)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | A solution of 70.0 mg of methyl 4-(3-{4-[3-(5,5-dimethyl-1,3-dioxan-2-yl)propoxy]-phenyl}propoxy)-3-({[3-(methoxycarbonyl)cyclohexyl]amino}carbonyl)benzoate in 1 ml each of methanol, THF and 2 molar sodium hydroxide solution is stirred at a temperature of 60° C. for 2 hours. Then 1.1 ml of 2 molar hydrochloric acid are... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.C1COCOC1.C1CCCCC1 | Other | CO.[OH-].[Na+].C1CCOC1 | null | 15 | COC(=O)c1ccc(OCCCc2ccc(OCCCC3OCC(C)(C)CO3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1>CO.[OH-].[Na+].C1CCOC1>COC(=O)c1ccc(OCCCc2ccc(OCCCC3OCC(C)(C)CO3)cc2)c(C(=O)NC2CCCC(C(=O)O)C2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a247ab81676a44daae99723d01250007 | CCCOc1ccc(CCl)cc1.COC(=O)c1ccc(OCCCc2ccc(O)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1>>CCCOc1ccc(COc2ccc(CCCOc3ccc(C(=O)OC)cc3C(=O)NC3CCCC(C(=O)OC)C3)cc2)cc1 | OC1=CC=C(C=C1)CCCOC1=C(C=C(C(=O)OC)C=C1)C(=O)NC1CC(CCC1)C(=O)OC.ClCC1=CC=C(C=C1)OCCC>>COC(=O)C1CC(CCC1)NC(=O)C=1C=C(C(=O)OC)C=CC1OCCCC1=CC=C(C=C1)OCC1=CC=C(C=C1)OCCC | Cl[CH2:9][c:8]1[cH:7][cH:6][c:5]([O:4][CH2:3][CH2:2][CH3:1])[cH:45][cH:44]1.[OH:10][c:11]1[cH:12][cH:13][c:14]([CH2:15][CH2:16][CH2:17][O:18][c:19]2[cH:20][cH:21][c:22]([C:23](=[O:24])[O:25][CH3:26])[cH:27][c:28]2[C:29](=[O:30])[NH:31][CH:32]2[CH2:33][CH2:34][CH2:35][CH:36]([C:37](=[O:38])[O:39][CH3:40])[CH2:41]2)[cH:4... | CCCOc1ccc(CCl)cc1.COC(=O)c1ccc(OCCCc2ccc(O)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | CCCOc1ccc(COc2ccc(CCCOc3ccc(C(=O)OC)cc3C(=O)NC3CCCC(C(=O)OC)C3)cc2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(NC1CCCCC1)c1ccccc1OCCCc1ccc(OCc2ccccc2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | null | [] | null | null | null | null | Methyl 3-({[3-(methoxycarbonyl)cyclohexyl]amino}carbonyl)-4-(3-{4-[(4-propoxybenzyl)oxy]phenyl}propoxy)benzoate is prepared in analogy to the process described in Example 34 from methyl 4-[3-(4-hydroxyphenyl)propoxy]-3-({[3-(methoxycarbonyl)cyclohexyl]amino}carbonyl)benzoate and 1-(chloromethyl)-4-propoxybenzene.
Condi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CCCCC1 | HCl | null | null | null | CCCOc1ccc(CCl)cc1.COC(=O)c1ccc(OCCCc2ccc(O)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1>>CCCOc1ccc(COc2ccc(CCCOc3ccc(C(=O)OC)cc3C(=O)NC3CCCC(C(=O)OC)C3)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-be05247ab3ed4304ab69c202b3792640 | COC(=O)c1ccc(OCCCc2ccc(O)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1.ClCc1ccc(OCC2CC2)cc1>>COC(=O)c1ccc(OCCCc2ccc(OCc3ccc(OCC4CC4)cc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | OC1=CC=C(C=C1)CCCOC1=C(C=C(C(=O)OC)C=C1)C(=O)NC1CC(CCC1)C(=O)OC.ClCC1=CC=C(C=C1)OCC1CC1>>C1(CC1)COC1=CC=C(COC2=CC=C(C=C2)CCCOC2=C(C=C(C(=O)OC)C=C2)C(=O)NC2CC(CCC2)C(=O)OC)C=C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][CH2:12][c:13]2[cH:14][cH:15][c:16]([OH:17])[cH:30][cH:31]2)[c:32]([C:33](=[O:34])[NH:35][CH:36]2[CH2:37][CH2:38][CH2:39][CH:40]([C:41](=[O:42])[O:43][CH3:44])[CH2:45]2)[cH:46]1.Cl[CH2:18][c:19]1[cH:20][cH:21][c:22]([O:23][CH2:24][CH:25]2[CH2:26][CH2... | COC(=O)c1ccc(OCCCc2ccc(O)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1.ClCc1ccc(OCC2CC2)cc1 | COC(=O)c1ccc(OCCCc2ccc(OCc3ccc(OCC4CC4)cc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(NC1CCCCC1)c1ccccc1OCCCc1ccc(OCc2ccc(OCC3CC3)cc2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | null | [] | null | null | null | null | Methyl 4-[3-(4-{[4-(cyclopropylmethoxy)benzyl]oxy}phenyl)propoxy]-3-({[3-(methoxycarbonyl)cyclohexyl]amino}carbonyl)benzoate is prepared in analogy to the process described in Example 34 from methyl 4-[3-(4-hydroxyphenyl)propoxy]-3-({[3-(methoxycarbonyl)cyclohexyl]amino}carbonyl)benzoate and 1-(chloromethyl)-4-(cyclopr... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CC1.C1CCCCC1 | HCl | null | null | null | COC(=O)c1ccc(OCCCc2ccc(O)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1.ClCc1ccc(OCC2CC2)cc1>>COC(=O)c1ccc(OCCCc2ccc(OCc3ccc(OCC4CC4)cc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f7c7f55d484449249aa033c672f4fe67 | COC(=O)c1ccc(OCCCc2ccc(O)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1.ClCc1ccc(Oc2ccccc2)cc1>>COC(=O)c1ccc(OCCCc2ccc(OCc3ccc(Oc4ccccc4)cc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | OC1=CC=C(C=C1)CCCOC1=C(C=C(C(=O)OC)C=C1)C(=O)NC1CC(CCC1)C(=O)OC.ClCC1=CC=C(C=C1)OC1=CC=CC=C1>>COC(=O)C1CC(CCC1)NC(=O)C=1C=C(C(=O)OC)C=CC1OCCCC1=CC=C(C=C1)OCC1=CC=C(C=C1)OC1=CC=CC=C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][CH2:12][c:13]2[cH:14][cH:15][c:16]([OH:17])[cH:32][cH:33]2)[c:34]([C:35](=[O:36])[NH:37][CH:38]2[CH2:39][CH2:40][CH2:41][CH:42]([C:43](=[O:44])[O:45][CH3:46])[CH2:47]2)[cH:48]1.Cl[CH2:18][c:19]1[cH:20][cH:21][c:22]([O:23][c:24]2[cH:25][cH:26][cH:27]... | COC(=O)c1ccc(OCCCc2ccc(O)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1.ClCc1ccc(Oc2ccccc2)cc1 | COC(=O)c1ccc(OCCCc2ccc(OCc3ccc(Oc4ccccc4)cc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(NC1CCCCC1)c1ccccc1OCCCc1ccc(OCc2ccc(Oc3ccccc3)cc2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | null | [] | null | null | null | null | Methyl 3-({[3-(methoxycarbonyl)cyclohexyl]amino}carbonyl)-4-(3-{4-[(4-phenoxybenzyl)oxy]phenyl}propoxy)benzoate is prepared in analogy to the process described in Example 34 from methyl 4-[3-(4-hydroxyphenyl)propoxy]-3-({[3-(methoxycarbonyl)cyclohexyl]amino}carbonyl)benzoate and 1-(chloromethyl)-4-phenoxybenzene.
Condi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.C1CCCCC1 | HCl | null | null | null | COC(=O)c1ccc(OCCCc2ccc(O)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1.ClCc1ccc(Oc2ccccc2)cc1>>COC(=O)c1ccc(OCCCc2ccc(OCc3ccc(Oc4ccccc4)cc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-30761e5bf07a493e9f71192d55e3db2a | CC(C)COc1ccc(CCl)cc1.COC(=O)c1ccc(OCCCc2ccc(O)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1>>COC(=O)c1ccc(OCCCc2ccc(OCc3ccc(OCC(C)C)cc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | OC1=CC=C(C=C1)CCCOC1=C(C=C(C(=O)OC)C=C1)C(=O)NC1CC(CCC1)C(=O)OC.ClCC1=CC=C(C=C1)OCC(C)C>>C(C(C)C)OC1=CC=C(COC2=CC=C(C=C2)CCCOC2=C(C=C(C(=O)OC)C=C2)C(=O)NC2CC(CCC2)C(=O)OC)C=C1 | Cl[CH2:18][c:19]1[cH:20][cH:21][c:22]([O:23][CH2:24][CH:25]([CH3:26])[CH3:27])[cH:28][cH:29]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][CH2:12][c:13]2[cH:14][cH:15][c:16]([OH:17])[cH:30][cH:31]2)[c:32]([C:33](=[O:34])[NH:35][CH:36]2[CH2:37][CH2:38][CH2:39][CH:40]([C:41](=[O:42])[O:43][CH3:4... | CC(C)COc1ccc(CCl)cc1.COC(=O)c1ccc(OCCCc2ccc(O)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | COC(=O)c1ccc(OCCCc2ccc(OCc3ccc(OCC(C)C)cc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(NC1CCCCC1)c1ccccc1OCCCc1ccc(OCc2ccccc2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | null | [] | null | null | null | null | Methyl 4-(3-{4-[(4-isobutoxybenzyl)oxy]phenyl}propoxy)-3-({[3-(methoxycarbonyl)cyclohexyl]amino}carbonyl)benzoate is prepared in analogy to the process described in Example 34 from methyl 4-[3-(4-hydroxyphenyl)propoxy]-3-({[3-(methoxycarbonyl)cyclohexyl]amino}carbonyl)benzoate and 1-(chloromethyl)-4-isobutoxybenzene.
C... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CCCCC1 | HCl | null | null | null | CC(C)COc1ccc(CCl)cc1.COC(=O)c1ccc(OCCCc2ccc(O)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1>>COC(=O)c1ccc(OCCCc2ccc(OCc3ccc(OCC(C)C)cc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8acc657d057242aabcab08b6c125f834 | COC(=O)c1ccc(OCCCc2ccc(O)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1.ClCc1ccc2c(c1)CCCC2>>COC(=O)c1ccc(OCCCc2ccc(OCc3ccc4c(c3)CCCC4)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | OC1=CC=C(C=C1)CCCOC1=C(C=C(C(=O)OC)C=C1)C(=O)NC1CC(CCC1)C(=O)OC.ClCC=1C=C2CCCCC2=CC1>>COC(=O)C1CC(CCC1)NC(=O)C=1C=C(C(=O)OC)C=CC1OCCCC1=CC=C(C=C1)OCC1=CC=2CCCCC2C=C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][CH2:12][c:13]2[cH:14][cH:15][c:16]([OH:17])[cH:29][cH:30]2)[c:31]([C:32](=[O:33])[NH:34][CH:35]2[CH2:36][CH2:37][CH2:38][CH:39]([C:40](=[O:41])[O:42][CH3:43])[CH2:44]2)[cH:45]1.Cl[CH2:18][c:19]1[cH:20][cH:21][c:22]2[c:23]([cH:24]1)[CH2:25][CH2:26][C... | COC(=O)c1ccc(OCCCc2ccc(O)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1.ClCc1ccc2c(c1)CCCC2 | COC(=O)c1ccc(OCCCc2ccc(OCc3ccc4c(c3)CCCC4)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(NC1CCCCC1)c1ccccc1OCCCc1ccc(OCc2ccc3c(c2)CCCC3)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | null | [] | null | null | null | null | Methyl 3-({[3-(methoxycarbonyl)cyclohexyl]amino}carbonyl)-4-{3-[4-(5,6,7,8-tetrahydronaphthalen-2-ylmethoxy)phenyl]propoxy}benzoate is prepared in analogy to the process described in Example 34 from methyl 4-[3-(4-hydroxyphenyl)-propoxy]-3-({[3-(methoxycarbonyl)cyclohexyl]amino}carbonyl)benzoate and 6-(chloromethyl)-1,... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CCCC2.C1CCCCC1 | HCl | null | null | null | COC(=O)c1ccc(OCCCc2ccc(O)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1.ClCc1ccc2c(c1)CCCC2>>COC(=O)c1ccc(OCCCc2ccc(OCc3ccc4c(c3)CCCC4)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-180cd65eac5141c888b5262c612d7bec | COC(=O)c1ccc(OCCCc2ccc(O)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1.ClCc1ccc(C2CCCCC2)cc1>>COC(=O)c1ccc(OCCCc2ccc(OCc3ccc(C4CCCCC4)cc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | OC1=CC=C(C=C1)CCCOC1=C(C=C(C(=O)OC)C=C1)C(=O)NC1CC(CCC1)C(=O)OC.ClCC1=CC=C(C=C1)C1CCCCC1>>C1(CCCCC1)C1=CC=C(COC2=CC=C(C=C2)CCCOC2=C(C=C(C(=O)OC)C=C2)C(=O)NC2CC(CCC2)C(=O)OC)C=C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][CH2:12][c:13]2[cH:14][cH:15][c:16]([OH:17])[cH:31][cH:32]2)[c:33]([C:34](=[O:35])[NH:36][CH:37]2[CH2:38][CH2:39][CH2:40][CH:41]([C:42](=[O:43])[O:44][CH3:45])[CH2:46]2)[cH:47]1.Cl[CH2:18][c:19]1[cH:20][cH:21][c:22]([CH:23]2[CH2:24][CH2:25][CH2:26][C... | COC(=O)c1ccc(OCCCc2ccc(O)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1.ClCc1ccc(C2CCCCC2)cc1 | COC(=O)c1ccc(OCCCc2ccc(OCc3ccc(C4CCCCC4)cc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(NC1CCCCC1)c1ccccc1OCCCc1ccc(OCc2ccc(C3CCCCC3)cc2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | null | [] | null | null | null | null | Methyl 4-(3-{4-[(4-cyclohexylbenzyl)oxy]phenyl}propoxy)-3-({[3-(methoxycarbonyl)cyclohexyl]amino}carbonyl)benzoate is prepared in analogy to the process described in Example 34 from methyl 4-[3-(4-hydroxyphenyl)propoxy]-3-({[3-(methoxycarbonyl)cyclohexyl]amino}carbonyl)benzoate and 1-(chloromethyl)-4-cyclohexylbenzene.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CCCCC1.C1CCCCC1 | HCl | null | null | null | COC(=O)c1ccc(OCCCc2ccc(O)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1.ClCc1ccc(C2CCCCC2)cc1>>COC(=O)c1ccc(OCCCc2ccc(OCc3ccc(C4CCCCC4)cc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d9674f46eebf44a3a229f43481722c2b | CCOC(=O)c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)O)c1.COC(=O)[C@H]1CC[C@@H](N)C1>>CCOC(=O)c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)N[C@@H]2CC[C@H](C(=O)OC)C2)c1 | C1(=CC=C(C=C1)COC1=CC=C(C=C1)CCCOC1=C(C(=O)O)C=C(C=C1)C(=O)OCC)C1=CC=CC=C1.Cl.N[C@H]1C[C@H](CC1)C(=O)OC>>C1(=CC=C(C=C1)COC1=CC=C(C=C1)CCCOC1=C(C=C(C(=O)OCC)C=C1)C(=O)N[C@H]1C[C@H](CC1)C(=O)OC)C1=CC=CC=C1 | O[C:35]([c:34]1[c:9]([O:10][CH2:11][CH2:12][CH2:13][c:14]2[cH:15][cH:16][c:17]([O:18][CH2:19][c:20]3[cH:21][cH:22][c:23](-[c:24]4[cH:25][cH:26][cH:27][cH:28][cH:29]4)[cH:30][cH:31]3)[cH:32][cH:33]2)[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:47]1)=[O:36].[NH2:37][C@@H:38]1[CH2:39][CH2:40][C@H:41]([C:42](=[O:... | CCOC(=O)c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)O)c1.COC(=O)[C@H]1CC[C@@H](N)C1 | CCOC(=O)c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)N[C@@H]2CC[C@H](C(=O)OC)C2)c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NC1CCCC1)c1ccccc1OCCCc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7](-[NH2;D1;+0:8])-[C:9]>>[C:6]-[C:7](-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:9] | null | [] | null | null | null | null | Preparation takes place in analogy to Example 5 from 2-{3-[4-(1,1′-biphenyl-4-yl-methoxy)phenyl]propoxy}-5-(ethoxycarbonyl)benzoic acid and methyl (1S,3R)-3-aminocyclopentanecarboxylate hydrochloride.
Conditions: See reaction.notes.procedure_details.
Workup: Preparation | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.C1CCCC1 | HO- | null | null | null | CCOC(=O)c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)O)c1.COC(=O)[C@H]1CC[C@@H](N)C1>>CCOC(=O)c1ccc(OCCCc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)N[C@@H]2CC[C@H](C(=O)OC)C2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1b95eed16c7a4451851b066b5d82da3d | COC(=O)c1ccc(OCCCc2ccc(O)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1.FC(F)(F)Oc1ccc(CCl)cc1>>COC(=O)c1ccc(OCCCc2ccc(OCc3ccc(OC(F)(F)F)cc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | OC1=CC=C(C=C1)CCCOC1=C(C=C(C(=O)OC)C=C1)C(=O)NC1CC(CCC1)C(=O)OC.ClCC1=CC=C(C=C1)OC(F)(F)F>>COC(=O)C1CC(CCC1)NC(=O)C=1C=C(C(=O)OC)C=CC1OCCCC1=CC=C(C=C1)OCC1=CC=C(C=C1)OC(F)(F)F | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][CH2:12][c:13]2[cH:14][cH:15][c:16]([OH:17])[cH:30][cH:31]2)[c:32]([C:33](=[O:34])[NH:35][CH:36]2[CH2:37][CH2:38][CH2:39][CH:40]([C:41](=[O:42])[O:43][CH3:44])[CH2:45]2)[cH:46]1.Cl[CH2:18][c:19]1[cH:20][cH:21][c:22]([O:23][C:24]([F:25])([F:26])[F:27]... | COC(=O)c1ccc(OCCCc2ccc(O)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1.FC(F)(F)Oc1ccc(CCl)cc1 | COC(=O)c1ccc(OCCCc2ccc(OCc3ccc(OC(F)(F)F)cc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(NC1CCCCC1)c1ccccc1OCCCc1ccc(OCc2ccccc2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | null | [] | null | null | null | null | Methyl 3-({[3-(methoxycarbonyl)cyclohexyl]amino}carbonyl)-4-[3-(4-{[4-(trifluoromethoxy)benzyl]oxy}phenyl)propoxy]benzoate is prepared in analogy to the process described in Example 34 from methyl 4-[3-(4-hydroxyphenyl)propoxy]-3-({[3-(methoxycarbonyl)cyclohexyl]amino}carbonyl)benzoate and 1-(chloromethyl)-4-trifluorom... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CCCCC1 | HCl | null | null | null | COC(=O)c1ccc(OCCCc2ccc(O)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1.FC(F)(F)Oc1ccc(CCl)cc1>>COC(=O)c1ccc(OCCCc2ccc(OCc3ccc(OC(F)(F)F)cc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1eec3f42f5ac492aa0ff2f92ef5f3933 | COC(=O)c1ccc(OCCCc2ccc(O)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1.Clc1ccc(CCCBr)cc1>>COC(=O)c1ccc(OCCCc2ccc(OCCCc3ccc(Cl)cc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | OC1=CC=C(C=C1)CCCOC1=C(C=C(C(=O)OC)C=C1)C(=O)NC1CC(CCC1)C(=O)OC.BrCCCC1=CC=C(C=C1)Cl>>ClC1=CC=C(C=C1)CCCOC1=CC=C(C=C1)CCCOC1=C(C=C(C(=O)OC)C=C1)C(=O)NC1CC(CCC1)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][CH2:12][c:13]2[cH:14][cH:15][c:16]([OH:17])[cH:28][cH:29]2)[c:30]([C:31](=[O:32])[NH:33][CH:34]2[CH2:35][CH2:36][CH2:37][CH:38]([C:39](=[O:40])[O:41][CH3:42])[CH2:43]2)[cH:44]1.Br[CH2:18][CH2:19][CH2:20][c:21]1[cH:22][cH:23][c:24]([Cl:25])[cH:26][cH... | COC(=O)c1ccc(OCCCc2ccc(O)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1.Clc1ccc(CCCBr)cc1 | COC(=O)c1ccc(OCCCc2ccc(OCCCc3ccc(Cl)cc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(NC1CCCCC1)c1ccccc1OCCCc1ccc(OCCCc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | Methyl 4-(3-{4-[3-(4-chlorophenyl)propoxy]phenyl}propoxy)-3-({[3-(methoxycarbonyl)cyclohexyl]amino}carbonyl)benzoate is prepared in analogy to the process described in Example 34 from methyl 4-[3-(4-hydroxyphenyl)propoxy]-3-({[3-(methoxycarbonyl)cyclohexyl]amino}carbonyl)benzoate and 1-(3-bromopropyl)-4-chlorobenzene.
... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CCCCC1 | HBr | null | null | null | COC(=O)c1ccc(OCCCc2ccc(O)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1.Clc1ccc(CCCBr)cc1>>COC(=O)c1ccc(OCCCc2ccc(OCCCc3ccc(Cl)cc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ba946eb641c849c2b4a88f9bf35c44f4 | BrCCCc1ccc(OCCCC2CCCCC2)cc1.CCOC(=O)CC1CN(C(=O)c2cc(C(=O)OC)ccc2O)C1>>CCOC(=O)CC1CN(C(=O)c2cc(C(=O)OC)ccc2OCCCc2ccc(OCCCC3CCCCC3)cc2)C1 | C(C)OC(CC1CN(C1)C(=O)C=1C=C(C(=O)OC)C=CC1O)=O.BrCCCC1=CC=C(C=C1)OCCCC1CCCCC1>>C1(CCCCC1)CCCOC1=CC=C(C=C1)CCCOC1=C(C=C(C(=O)OC)C=C1)C(=O)N1CC(C1)CC(=O)OCC | Br[CH2:23][CH2:24][CH2:25][c:26]1[cH:27][cH:28][c:29]([O:30][CH2:31][CH2:32][CH2:33][CH:34]2[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]2)[cH:40][cH:41]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]1[CH2:8][N:9]([C:10](=[O:11])[c:12]2[cH:13][c:14]([C:15](=[O:16])[O:17][CH3:18])[cH:19][cH:20][c:21]2[OH:22])[CH2:42]1>>[CH3:... | BrCCCc1ccc(OCCCC2CCCCC2)cc1.CCOC(=O)CC1CN(C(=O)c2cc(C(=O)OC)ccc2O)C1 | CCOC(=O)CC1CN(C(=O)c2cc(C(=O)OC)ccc2OCCCc2ccc(OCCCC3CCCCC3)cc2)C1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(c1ccccc1OCCCc1ccc(OCCCC2CCCCC2)cc1)N1CCC1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[#7:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:10] | null | [] | null | null | null | null | Preparation takes place in analogy to the process described in Example 22 from methyl 3-{[3-(2-ethoxy-2-oxoethyl)azetidin-1-yl]carbonyl}-4-hydroxybenzoate and 1-(3-bromopropyl)-4-(3-cyclohexylpropoxy)benzene.
Conditions: See reaction.notes.procedure_details.
Workup: Preparation | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | C1C[NH]C1.c1ccccc1.c1ccccc1.C1CCCCC1 | HBr | null | null | null | BrCCCc1ccc(OCCCC2CCCCC2)cc1.CCOC(=O)CC1CN(C(=O)c2cc(C(=O)OC)ccc2O)C1>>CCOC(=O)CC1CN(C(=O)c2cc(C(=O)OC)ccc2OCCCc2ccc(OCCCC3CCCCC3)cc2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-985b55b181f14481821c27b015ed89ad | COC(=O)c1ccc(O)c(C(=O)NC2CCCC(C(=O)OC)C2)c1.ICCCc1ccc(CCCCCOc2ccccc2)cc1>>COC(=O)c1ccc(OCCCc2ccc(CCCCCOc3ccccc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | OC1=C(C=C(C(=O)OC)C=C1)C(=O)NC1CC(CCC1)C(=O)OC.ICCCC1=CC=C(C=C1)CCCCCOC1=CC=CC=C1>>COC(=O)C1CC(CCC1)NC(=O)C=1C=C(C(=O)OC)C=CC1OCCCC1=CC=C(C=C1)CCCCCOC1=CC=CC=C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:31]([C:32](=[O:33])[NH:34][CH:35]2[CH2:36][CH2:37][CH2:38][CH:39]([C:40](=[O:41])[O:42][CH3:43])[CH2:44]2)[cH:45]1.I[CH2:10][CH2:11][CH2:12][c:13]1[cH:14][cH:15][c:16]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[cH... | COC(=O)c1ccc(O)c(C(=O)NC2CCCC(C(=O)OC)C2)c1.ICCCc1ccc(CCCCCOc2ccccc2)cc1 | COC(=O)c1ccc(OCCCc2ccc(CCCCCOc3ccccc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(NC1CCCCC1)c1ccccc1OCCCc1ccc(CCCCCOc2ccccc2)cc1 | I-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[#7:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:10] | null | [] | null | null | null | null | Preparation takes place in analogy to Example 22 from the (+)-B-enantiomer of methyl 4-hydroxy-3-({[3-(methoxycarbonyl)cyclohexyl]amino}carbonyl)benzoate (see Example IX, method 2) and 1-(3-iodopropyl)-4-(5-phenoxypentyl)benzene.
Conditions: See reaction.notes.procedure_details.
Workup: Preparation | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CCCCC1 | HI | null | null | null | COC(=O)c1ccc(O)c(C(=O)NC2CCCC(C(=O)OC)C2)c1.ICCCc1ccc(CCCCCOc2ccccc2)cc1>>COC(=O)c1ccc(OCCCc2ccc(CCCCCOc3ccccc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-51230e606b3b4fce94023cc2d0eabd29 | CCOC(=O)CC1C[NH2+]C1.CCOC(=O)c1ccc(OCCCc2ccc(OCCCCOc3ccccc3)cc2)c(C(=O)O)c1>>CCOC(=O)CC1CN(C(=O)c2cc(C(=O)OCC)ccc2OCCCc2ccc(OCCCCOc3ccccc3)cc2)C1 | [Cl-].C(C)OC(CC1C[NH2+]C1)=O.C(C)OC(=O)C=1C=CC(=C(C(=O)O)C1)OCCCC1=CC=C(C=C1)OCCCCOC1=CC=CC=C1>>C(C)OC(CC1CN(C1)C(=O)C=1C=C(C(=O)OCC)C=CC1OCCCC1=CC=C(C=C1)OCCCCOC1=CC=CC=C1)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]1[CH2:8][NH2+:9][CH2:45]1.O[C:10](=[O:11])[c:12]1[cH:13][c:14]([C:15](=[O:16])[O:17][CH2:18][CH3:19])[cH:20][cH:21][c:22]1[O:23][CH2:24][CH2:25][CH2:26][c:27]1[cH:28][cH:29][c:30]([O:31][CH2:32][CH2:33][CH2:34][CH2:35][O:36][c:37]2[cH:38][cH:39][cH:40][cH:41][cH:42]2)[cH:43]... | CCOC(=O)CC1C[NH2+]C1.CCOC(=O)c1ccc(OCCCc2ccc(OCCCCOc3ccccc3)cc2)c(C(=O)O)c1 | CCOC(=O)CC1CN(C(=O)c2cc(C(=O)OCC)ccc2OCCCc2ccc(OCCCCOc3ccccc3)cc2)C1 | null | null | null | Acylation | Schotten-Baumann_amide | 9b107daf57279720267898f8214c3c09a3a66e8e6d8348e838ee6aa0b4e96cc9 | c895b6715381a452955f31637da0bb73988a49399b1e84d4b4b9df1a85d0ae0b | O=C(c1ccccc1OCCCc1ccc(OCCCCOc2ccccc2)cc1)N1CCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]1-[C:7]-[C:8]-[NH2+;D2:9]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:6]-[C:7]-[C:8]-1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | Preparation takes place in analogy to Example IX, method 3, from 3-(2-ethoxy-2-oxoethyl)azetidinium chloride and 5-(ethoxycarbonyl)-2-{3-[4-(4-phenoxybutoxy)-phenyl]propoxy}benzoic acid.
Conditions: See reaction.notes.procedure_details.
Workup: Preparation | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Tertiary amide | C1C[NH+]C1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CCOC(=O)CC1C[NH2+]C1.CCOC(=O)c1ccc(OCCCc2ccc(OCCCCOc3ccccc3)cc2)c(C(=O)O)c1>>CCOC(=O)CC1CN(C(=O)c2cc(C(=O)OCC)ccc2OCCCc2ccc(OCCCCOc3ccccc3)cc2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7b23d17ccdeb4338becb61ce1f456aba | BrCCOc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1.COC(=O)c1ccc(O)c(C(=O)NC2CCCC(C(=O)OC)C2)c1>>COC(=O)c1ccc(OCCOc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | OC1=C(C=C(C(=O)OC)C=C1)C(=O)NC1CC(CCC1)C(=O)OC.BrCCOC1=CC=C(OCC2=CC=C(C=C2)C2=CC=CC=C2)C=C1>>C1(=CC=C(C=C1)COC1=CC=C(OCCOC2=C(C=C(C(=O)OC)C=C2)C(=O)NC2CC(CCC2)C(=O)OC)C=C1)C1=CC=CC=C1 | Br[CH2:10][CH2:11][O:12][c:13]1[cH:14][cH:15][c:16]([O:17][CH2:18][c:19]2[cH:20][cH:21][c:22](-[c:23]3[cH:24][cH:25][cH:26][cH:27][cH:28]3)[cH:29][cH:30]2)[cH:31][cH:32]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:33]([C:34](=[O:35])[NH:36][CH:37]2[CH2:38][CH2:39][CH2:40][CH:41]([C:42](=[O:43])[O:44][CH... | BrCCOc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1.COC(=O)c1ccc(O)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | COC(=O)c1ccc(OCCOc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(NC1CCCCC1)c1ccccc1OCCOc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[#7:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[#7:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C:2]-[#8:3]):[c:10] | null | [] | null | null | null | null | Preparation takes place in analogy to Example 22 from the (+)-B-enantiomer of methyl 4-hydroxy-3-({[3-(methoxycarbonyl)cyclohexyl]amino}carbonyl)benzoate (see Example IX, method 2) and 4-{[4-(2-bromoethoxy)phenoxy]methyl}biphenyl.
Conditions: See reaction.notes.procedure_details.
Workup: Preparation | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.C1CCCCC1 | HBr | null | null | null | BrCCOc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1.COC(=O)c1ccc(O)c(C(=O)NC2CCCC(C(=O)OC)C2)c1>>COC(=O)c1ccc(OCCOc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-03c1f59eee2746c194b6039abe4c9a88 | COC(=O)c1ccc(O)c(C(=O)NC2CCCC(C(=O)OC)C2)c1.ICCCc1ccc(CCc2ccc(-c3ccccc3)cc2)cc1>>COC(=O)c1ccc(OCCCc2ccc(CCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | OC1=C(C=C(C(=O)OC)C=C1)C(=O)NC1CC(CCC1)C(=O)OC.ICCCC1=CC=C(C=C1)CCC1=CC=C(C=C1)C1=CC=CC=C1>>C1(=CC=C(C=C1)CCC1=CC=C(C=C1)CCCOC1=C(C=C(C(=O)OC)C=C1)C(=O)NC1CC(CCC1)C(=O)OC)C1=CC=CC=C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:33]([C:34](=[O:35])[NH:36][CH:37]2[CH2:38][CH2:39][CH2:40][CH:41]([C:42](=[O:43])[O:44][CH3:45])[CH2:46]2)[cH:47]1.I[CH2:10][CH2:11][CH2:12][c:13]1[cH:14][cH:15][c:16]([CH2:17][CH2:18][c:19]2[cH:20][cH:21][c:22](-[c:23]3[cH:24][cH:25][cH:26][cH:27][cH:28]3)[cH:... | COC(=O)c1ccc(O)c(C(=O)NC2CCCC(C(=O)OC)C2)c1.ICCCc1ccc(CCc2ccc(-c3ccccc3)cc2)cc1 | COC(=O)c1ccc(OCCCc2ccc(CCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(NC1CCCCC1)c1ccccc1OCCCc1ccc(CCc2ccc(-c3ccccc3)cc2)cc1 | I-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[#7:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:10] | null | [] | null | null | null | null | Preparation takes place in analogy to Example 22 from the (+)-B-enantiomer of methyl 4-hydroxy-3-({[3-(methoxycarbonyl)cyclohexyl]amino}carbonyl)benzoate (see Example IX, method 2) and 4-{2-[4-(3-iodopropyl)phenyl]ethyl}biphenyl.
Conditions: See reaction.notes.procedure_details.
Workup: Preparation | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.C1CCCCC1 | HI | null | null | null | COC(=O)c1ccc(O)c(C(=O)NC2CCCC(C(=O)OC)C2)c1.ICCCc1ccc(CCc2ccc(-c3ccccc3)cc2)cc1>>COC(=O)c1ccc(OCCCc2ccc(CCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-699105e9fcb045f0963202081b03dceb | BrCCOc1ccc(OCCCCOc2ccccc2)cc1.COC(=O)c1ccc(O)c(C(=O)NC2CCCC(C(=O)OC)C2)c1>>COC(=O)c1ccc(OCCOc2ccc(OCCCCOc3ccccc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | OC1=C(C=C(C(=O)OC)C=C1)C(=O)NC1CC(CCC1)C(=O)OC.BrCCOC1=CC=C(C=C1)OCCCCOC1=CC=CC=C1>>COC(=O)C1CC(CCC1)NC(=O)C=1C=C(C(=O)OC)C=CC1OCCOC1=CC=C(C=C1)OCCCCOC1=CC=CC=C1 | Br[CH2:10][CH2:11][O:12][c:13]1[cH:14][cH:15][c:16]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[cH:29][cH:30]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:31]([C:32](=[O:33])[NH:34][CH:35]2[CH2:36][CH2:37][CH2:38][CH:39]([C:40](=[O:41])[O:42][CH3:43])[CH2:44]2... | BrCCOc1ccc(OCCCCOc2ccccc2)cc1.COC(=O)c1ccc(O)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | COC(=O)c1ccc(OCCOc2ccc(OCCCCOc3ccccc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(NC1CCCCC1)c1ccccc1OCCOc1ccc(OCCCCOc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[#7:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[#7:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C:2]-[#8:3]):[c:10] | null | [] | null | null | null | null | Preparation takes place in analogy to Example 22 from the (+)-B-enantiomer of methyl 4-hydroxy-3-({[3-(methoxycarbonyl)cyclohexyl]amino}carbonyl)benzoate (see Example IX, method 2) and 1-(2-bromoethoxy)-4-(4-phenoxybutoxy)benzene.
Conditions: See reaction.notes.procedure_details.
Workup: Preparation | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CCCCC1 | HBr | null | null | null | BrCCOc1ccc(OCCCCOc2ccccc2)cc1.COC(=O)c1ccc(O)c(C(=O)NC2CCCC(C(=O)OC)C2)c1>>COC(=O)c1ccc(OCCOc2ccc(OCCCCOc3ccccc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ceef8fa19ccd4ee39159e2df53466ff3 | COC(=O)c1ccc(O)c(C(=O)NC2CCCC(C(=O)OC)C2)c1.ICCOc1ccc(/C=C\CCCOc2ccccc2)cc1>>COC(=O)c1ccc(OCCOc2ccc(/C=C\CCCOc3ccccc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | OC1=C(C=C(C(=O)OC)C=C1)C(=O)NC1CC(CCC1)C(=O)OC.ICCOC1=CC=C(C=C1)\C=C/CCCOC1=CC=CC=C1>>COC(=O)C1CC(CCC1)NC(=O)C=1C=C(C(=O)OC)C=CC1OCCOC1=CC=C(C=C1)\C=C/CCCOC1=CC=CC=C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:31]([C:32](=[O:33])[NH:34][CH:35]2[CH2:36][CH2:37][CH2:38][CH:39]([C:40](=[O:41])[O:42][CH3:43])[CH2:44]2)[cH:45]1.I[CH2:10][CH2:11][O:12][c:13]1[cH:14][cH:15][c:16](/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][O:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[cH:... | COC(=O)c1ccc(O)c(C(=O)NC2CCCC(C(=O)OC)C2)c1.ICCOc1ccc(/C=C\CCCOc2ccccc2)cc1 | COC(=O)c1ccc(OCCOc2ccc(/C=C\CCCOc3ccccc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(NC1CCCCC1)c1ccccc1OCCOc1ccc(/C=C\CCCOc2ccccc2)cc1 | I-[CH2;D2;+0:1]-[C:2]-[#8:3].[#7:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[#7:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C:2]-[#8:3]):[c:10] | null | [] | null | null | null | null | Preparation takes place in analogy to Example 22 from the (+)-B-enantiomer of methyl 4-hydroxy-3-({[3-(methoxycarbonyl)cyclohexyl]amino}carbonyl)benzoate (see Example IX, method 2) and 1-(2-iodoethoxy)-4-[(1Z)-5-phenoxypent-1-en-1-yl]benzene.
Conditions: See reaction.notes.procedure_details.
Workup: Preparation | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CCCCC1 | HI | null | null | null | COC(=O)c1ccc(O)c(C(=O)NC2CCCC(C(=O)OC)C2)c1.ICCOc1ccc(/C=C\CCCOc2ccccc2)cc1>>COC(=O)c1ccc(OCCOc2ccc(/C=C\CCCOc3ccccc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-74a13dcdc6fc49508a80380110c24b62 | BrCCOc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1.COC(=O)c1ccc(O)c(C(=O)N2CCC(C(=O)OC)CC2)c1>>COC(=O)c1ccc(OCCOc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)N2CCC(C(=O)OC)CC2)c1 | OC1=C(C(=O)N2CCC(CC2)C(=O)OC)C=C(C=C1)C(=O)OC.BrCCOC1=CC=C(OCC2=CC=C(C=C2)C2=CC=CC=C2)C=C1>>C1(=CC=C(C=C1)COC1=CC=C(OCCOC2=C(C(=O)N3CCC(CC3)C(=O)OC)C=C(C=C2)C(=O)OC)C=C1)C1=CC=CC=C1 | Br[CH2:10][CH2:11][O:12][c:13]1[cH:14][cH:15][c:16]([O:17][CH2:18][c:19]2[cH:20][cH:21][c:22](-[c:23]3[cH:24][cH:25][cH:26][cH:27][cH:28]3)[cH:29][cH:30]2)[cH:31][cH:32]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:33]([C:34](=[O:35])[N:36]2[CH2:37][CH2:38][CH:39]([C:40](=[O:41])[O:42][CH3:43])[CH2:44][C... | BrCCOc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1.COC(=O)c1ccc(O)c(C(=O)N2CCC(C(=O)OC)CC2)c1 | COC(=O)c1ccc(OCCOc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)N2CCC(C(=O)OC)CC2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(c1ccccc1OCCOc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1)N1CCCCC1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[#7:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[#7:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C:2]-[#8:3]):[c:10] | null | [] | null | null | null | null | Preparation takes place in analogy to Example 22 from methyl 1-[2-hydroxy-5-(methoxycarbonyl)benzoyl]piperidine-4-carboxylate and 4-{[4-(2-bromoethoxy)-phenoxy]methyl}biphenyl.
Conditions: See reaction.notes.procedure_details.
Workup: Preparation | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.C1CC[NH]CC1 | HBr | null | null | null | BrCCOc1ccc(OCc2ccc(-c3ccccc3)cc2)cc1.COC(=O)c1ccc(O)c(C(=O)N2CCC(C(=O)OC)CC2)c1>>COC(=O)c1ccc(OCCOc2ccc(OCc3ccc(-c4ccccc4)cc3)cc2)c(C(=O)N2CCC(C(=O)OC)CC2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-37c7b36e28f843359d9ba57c13f3bb80 | BrCC#Cc1ccc(OCCCCOc2ccccc2)cc1.COC(=O)c1ccc(O)c(C(=O)NC2CCCC(C(=O)OC)C2)c1>>COC(=O)c1ccc(OCC#Cc2ccc(OCCCCOc3ccccc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | OC1=C(C=C(C(=O)OC)C=C1)C(=O)NC1CC(CCC1)C(=O)OC.BrCC#CC1=CC=C(C=C1)OCCCCOC1=CC=CC=C1>>COC(=O)C1CC(CCC1)NC(=O)C=1C=C(C(=O)OC)C=CC1OCC#CC1=CC=C(C=C1)OCCCCOC1=CC=CC=C1 | Br[CH2:10][C:11]#[C:12][c:13]1[cH:14][cH:15][c:16]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[cH:29][cH:30]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:31]([C:32](=[O:33])[NH:34][CH:35]2[CH2:36][CH2:37][CH2:38][CH:39]([C:40](=[O:41])[O:42][CH3:43])[CH2:44]2)... | BrCC#Cc1ccc(OCCCCOc2ccccc2)cc1.COC(=O)c1ccc(O)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | COC(=O)c1ccc(OCC#Cc2ccc(OCCCCOc3ccccc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(NC1CCCCC1)c1ccccc1OCC#Cc1ccc(OCCCCOc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]#[C:3]-[c:4].[#7:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[OH;D1;+0:10]):[c:11]>>[#7:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[O;H0;D2;+0:10]-[CH2;D2;+0:1]-[C:2]#[C:3]-[c:4]):[c:11] | null | [] | null | null | null | null | Preparation takes place in analogy to Example 22 from the (+)-B-enantiomer of methyl 4-hydroxy-3-({[3-(methoxycarbonyl)cyclohexyl]amino}carbonyl)benzoate (see Example IX, method 2) and 1-(3-bromoprop-1-yn-1-yl)-4-(4-phenoxy-butoxy)benzene.
Conditions: See reaction.notes.procedure_details.
Workup: Preparation | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CCCCC1 | HBr | null | null | null | BrCC#Cc1ccc(OCCCCOc2ccccc2)cc1.COC(=O)c1ccc(O)c(C(=O)NC2CCCC(C(=O)OC)C2)c1>>COC(=O)c1ccc(OCC#Cc2ccc(OCCCCOc3ccccc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0425a617dbda455a9d71e2939d534bc4 | BrCCCc1ccc(OCC#CCOc2ccccc2)cc1.COC(=O)c1ccc(O)c(C(=O)NC2CCCC(C(=O)OC)C2)c1>>COC(=O)c1ccc(OCCCc2ccc(OCC#CCOc3ccccc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | OC1=C(C=C(C(=O)OC)C=C1)C(=O)NC1CC(CCC1)C(=O)OC.BrCCCC1=CC=C(C=C1)OCC#CCOC1=CC=CC=C1>>COC(=O)C1CC(CCC1)NC(=O)C=1C=C(C(=O)OC)C=CC1OCCCC1=CC=C(C=C1)OCC#CCOC1=CC=CC=C1 | Br[CH2:10][CH2:11][CH2:12][c:13]1[cH:14][cH:15][c:16]([O:17][CH2:18][C:19]#[C:20][CH2:21][O:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[cH:29][cH:30]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:31]([C:32](=[O:33])[NH:34][CH:35]2[CH2:36][CH2:37][CH2:38][CH:39]([C:40](=[O:41])[O:42][CH3:43])[CH2:44]2)... | BrCCCc1ccc(OCC#CCOc2ccccc2)cc1.COC(=O)c1ccc(O)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | COC(=O)c1ccc(OCCCc2ccc(OCC#CCOc3ccccc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(NC1CCCCC1)c1ccccc1OCCCc1ccc(OCC#CCOc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[#7:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:10] | null | [] | null | null | null | null | Preparation takes place in analogy to Example 22 from the (+)-B-enantiomer of methyl 4-hydroxy-3-({[3-(methoxycarbonyl)cyclohexyl]amino}carbonyl)benzoate (see Example IX, method 2) and 1-(3-bromopropyl)-4-[(4-phenoxybut-2-yn-1-yl)oxy]benzene.
Conditions: See reaction.notes.procedure_details.
Workup: Preparation | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CCCCC1 | HBr | null | null | null | BrCCCc1ccc(OCC#CCOc2ccccc2)cc1.COC(=O)c1ccc(O)c(C(=O)NC2CCCC(C(=O)OC)C2)c1>>COC(=O)c1ccc(OCCCc2ccc(OCC#CCOc3ccccc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ad8da8358e8c40f299d7765ce3973f6e | BrCCCc1ccc(/C=C\CCCOc2ccccc2)cc1.COC(=O)c1ccc(O)c(C(=O)NC2CCCC(C(=O)OC)C2)c1>>COC(=O)c1ccc(OCCCc2ccc(/C=C\CCCOc3ccccc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | OC1=C(C=C(C(=O)OC)C=C1)C(=O)NC1CC(CCC1)C(=O)OC.C1(=CC=CC=C1)OCCC\C=C/C1=CC=C(C=C1)CCCBr>>COC(=O)C1CC(CCC1)NC(=O)C=1C=C(C(=O)OC)C=CC1OCCCC1=CC=C(C=C1)\C=C/CCCOC1=CC=CC=C1 | Br[CH2:10][CH2:11][CH2:12][c:13]1[cH:14][cH:15][c:16](/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][O:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[cH:29][cH:30]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:31]([C:32](=[O:33])[NH:34][CH:35]2[CH2:36][CH2:37][CH2:38][CH:39]([C:40](=[O:41])[O:42][CH3:43])[CH2... | BrCCCc1ccc(/C=C\CCCOc2ccccc2)cc1.COC(=O)c1ccc(O)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | COC(=O)c1ccc(OCCCc2ccc(/C=C\CCCOc3ccccc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(NC1CCCCC1)c1ccccc1OCCCc1ccc(/C=C\CCCOc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[#7:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:10] | null | [] | null | null | null | null | Preparation takes place in analogy to Example 22 from the (+)-B-enantiomer of methyl 4-hydroxy-3-({[3-(methoxycarbonyl)cyclohexyl]amino}carbonyl)benzoate (see Example IX, method 2) and (4Z)-5-[4-(3-bromopropyl)phenyl]pent-4-en-1-yl phenyl ether.
Conditions: See reaction.notes.procedure_details.
Workup: Preparation | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CCCCC1 | HBr | null | null | null | BrCCCc1ccc(/C=C\CCCOc2ccccc2)cc1.COC(=O)c1ccc(O)c(C(=O)NC2CCCC(C(=O)OC)C2)c1>>COC(=O)c1ccc(OCCCc2ccc(/C=C\CCCOc3ccccc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0609e73e29a54275990065659001773f | BrCCCc1ccc(/C=C/CCCOc2ccccc2)cc1.COC(=O)c1ccc(O)c(C(=O)NC2CCCC(C(=O)OC)C2)c1>>COC(=O)c1ccc(OCCCc2ccc(/C=C/CCCOc3ccccc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | OC1=C(C=C(C(=O)OC)C=C1)C(=O)NC1CC(CCC1)C(=O)OC.C1(=CC=CC=C1)OCCC\C=C\C1=CC=C(C=C1)CCCBr>>COC(=O)C1CC(CCC1)NC(=O)C=1C=C(C(=O)OC)C=CC1OCCCC1=CC=C(C=C1)\C=C\CCCOC1=CC=CC=C1 | Br[CH2:10][CH2:11][CH2:12][c:13]1[cH:14][cH:15][c:16](/[CH:17]=[CH:18]/[CH2:19][CH2:20][CH2:21][O:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[cH:29][cH:30]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:31]([C:32](=[O:33])[NH:34][CH:35]2[CH2:36][CH2:37][CH2:38][CH:39]([C:40](=[O:41])[O:42][CH3:43])[CH2... | BrCCCc1ccc(/C=C/CCCOc2ccccc2)cc1.COC(=O)c1ccc(O)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | COC(=O)c1ccc(OCCCc2ccc(/C=C/CCCOc3ccccc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(NC1CCCCC1)c1ccccc1OCCCc1ccc(/C=C/CCCOc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[#7:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:10] | null | [] | null | null | null | null | Preparation takes place in analogy to Example 22 from the (+)-B-enantiomer of methyl 4-hydroxy-3-({[3-(methoxycarbonyl)cyclohexyl]amino}carbonyl)benzoate (see Example IX, method 2) and (4E)-5-[4-(3-bromopropyl)phenyl]pent-4-en-1-yl phenyl ether.
Conditions: See reaction.notes.procedure_details.
Workup: Preparation | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CCCCC1 | HBr | null | null | null | BrCCCc1ccc(/C=C/CCCOc2ccccc2)cc1.COC(=O)c1ccc(O)c(C(=O)NC2CCCC(C(=O)OC)C2)c1>>COC(=O)c1ccc(OCCCc2ccc(/C=C/CCCOc3ccccc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cbcad2f366db41a0b488719287a7310d | BrC/C=C/c1ccc(OCCCCOc2ccccc2)cc1.COC(=O)c1ccc(O)c(C(=O)NC2CCCC(C(=O)OC)C2)c1>>COC(=O)c1ccc(OC/C=C/c2ccc(OCCCCOc3ccccc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | OC1=C(C=C(C(=O)OC)C=C1)C(=O)NC1CC(CCC1)C(=O)OC.BrC/C=C/C1=CC=C(C=C1)OCCCCOC1=CC=CC=C1>>COC(=O)C1CC(CCC1)NC(=O)C=1C=C(C(=O)OC)C=CC1OC\C=C\C1=CC=C(C=C1)OCCCCOC1=CC=CC=C1 | Br[CH2:10]/[CH:11]=[CH:12]/[c:13]1[cH:14][cH:15][c:16]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[cH:29][cH:30]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:31]([C:32](=[O:33])[NH:34][CH:35]2[CH2:36][CH2:37][CH2:38][CH:39]([C:40](=[O:41])[O:42][CH3:43])[CH2:4... | BrC/C=C/c1ccc(OCCCCOc2ccccc2)cc1.COC(=O)c1ccc(O)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | COC(=O)c1ccc(OC/C=C/c2ccc(OCCCCOc3ccccc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(NC1CCCCC1)c1ccccc1OC/C=C/c1ccc(OCCCCOc2ccccc2)cc1 | Br-[CH2;D2;+0:1]/[C:2]=[C:3]/[c:4](:[c:5]):[c:6].[#7:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[OH;D1;+0:12]):[c:13]>>[#7:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[O;H0;D2;+0:12]-[CH2;D2;+0:1]/[C:2]=[C:3]/[c:4](:[c:5]):[c:6]):[c:13] | null | [] | null | null | null | null | Preparation takes place in analogy to Example 22 from the (+)-B-enantiomer of methyl 4-hydroxy-3-({[3-(methoxycarbonyl)cyclohexyl]amino}carbonyl)benzoate (see Example IX, method 2) and 1-[(1E)-3-bromoprop-1-en-1-yl]-4-(4-phenoxybutoxy)benzene.
Conditions: See reaction.notes.procedure_details.
Workup: Preparation | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CCCCC1 | HBr | null | null | null | BrC/C=C/c1ccc(OCCCCOc2ccccc2)cc1.COC(=O)c1ccc(O)c(C(=O)NC2CCCC(C(=O)OC)C2)c1>>COC(=O)c1ccc(OC/C=C/c2ccc(OCCCCOc3ccccc3)cc2)c(C(=O)NC2CCCC(C(=O)OC)C2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aaeeaec114344859b6d48f652674b390 | O=P(Cl)(Cl)Cl.O=c1[nH]cc(F)c(=O)[nH]1>>Fc1cnc(Cl)nc1Cl | FC=1C(NC(NC1)=O)=O.[Cl-].[Na+].P(Cl)(Cl)(Cl)(Cl)Cl.O=P(Cl)(Cl)Cl.P(Cl)(Cl)(Cl)(Cl)Cl.P(=O)(Cl)(Cl)Cl>>ClC1=NC=C(C(=N1)Cl)F | O=P(Cl)([Cl:6])[Cl:9].O=[c:5]1[nH:4][cH:3][c:2]([F:1])[c:8](=O)[nH:7]1>>[F:1][c:2]1[cH:3][n:4][c:5]([Cl:6])[n:7][c:8]1[Cl:9] | O=P(Cl)(Cl)Cl.O=c1[nH]cc(F)c(=O)[nH]1 | Fc1cnc(Cl)nc1Cl | null | null | null | Functional Group Interconversion | OtherReaction | 53f1491b612f3981c05f37e97f59f766695ac54324f2a2d459c7c6c0e64fea92 | 89023f2607b7fbe6acf264cf807d765723996f112da74c499f0176bdb5f1e3b7 | c1cncnc1 | Cl-P(=O)(-[Cl;H0;D1;+0:1])-[Cl;H0;D1;+0:2].O=[c;H0;D3;+0:3]1:[nH;D2;+0:4]:[c:5]:[c:6](-[F;D1;H0:7]):[c;H0;D3;+0:8](=O):[nH;D2;+0:9]:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:3]1:[n;H0;D2;+0:4]:[c:5]:[c:6](-[F;D1;H0:7]):[c;H0;D3;+0:8](-[Cl;H0;D1;+0:2]):[n;H0;D2;+0:9]:1 | null | [] | null | null | 1 | HOUR | To a dry reaction flask equipped with a stir bar and a reflux condenser was placed 5-fluorouracil (0.65 g, 5 mmol) followed by phosphorus oxychloride (POCl3) (1.53 g, 10 mmol). The resultant mixture was heated at 110° C. for 8 hours under a nitrogen atmosphere. The reaction was cooled to room temperature, phosphorus pe... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide.Aromatic halide | c1cncnc1 | c1cncnc1 | c1cncnc1 | HCl | null | null | 1 | O=P(Cl)(Cl)Cl.O=c1[nH]cc(F)c(=O)[nH]1>>Fc1cnc(Cl)nc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6d4458fbdd9443c2aa94591d82b6503f | Fc1cnc(Cl)nc1Cl.Nc1ccc2c(c1)OCCO2>>Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2 | ClC1=NC=C(C(=N1)Cl)F.N#N.C1OC=2C=C(N)C=CC2OC1.ClC1=NC=C(C(=N1)Cl)F.Cl>>ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F | Cl[c:8]1[c:2]([F:1])[cH:3][n:4][c:5]([Cl:6])[n:7]1.[NH2:9][c:10]1[cH:11][cH:12][c:13]2[c:14]([cH:15]1)[O:16][CH2:17][CH2:18][O:19]2>>[F:1][c:2]1[cH:3][n:4][c:5]([Cl:6])[n:7][c:8]1[NH:9][c:10]1[cH:11][cH:12][c:13]2[c:14]([cH:15]1)[O:16][CH2:17][CH2:18][O:19]2 | Fc1cnc(Cl)nc1Cl.Nc1ccc2c(c1)OCCO2 | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2 | null | null | O.CO | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ccc3c(c2)OCCO3)ncn1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[F;D1;H0:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[Cl;D1;H0:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[F;D1;H0:8]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[#7;a:2]:1 | 78 | [{"value": 78.0, "product": "ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | The reaction flask equipped with a magnetic stirring bar and a rubber septum (to prevent loss of 2,4-dichloro-5-fluoropyrimidine and N2 inlet was charged with 3,4-ethylenedioxyaniline (34 g, 225 mmol), MeOH (100 mL), H2O (300 mL) and 2,4-dichloro-5-fluoropyrimidine (25 g, 150 mmol). The reaction mixture was stirred at ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccc2c(c1)OCCO2 | HCl | O.CO | null | 1 | Fc1cnc(Cl)nc1Cl.Nc1ccc2c(c1)OCCO2>O.CO>Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a5353422f27043f69a560420861429ab | Fc1cnc(Cl)nc1Cl.Nc1ccc(N2CCN(Cc3ccccc3)CC2)cc1>>Fc1cnc(Cl)nc1Nc1ccc(N2CCN(Cc3ccccc3)CC2)cc1 | C(C1=CC=CC=C1)N1CCN(CC1)C1=CC=C(N)C=C1.ClC1=NC=C(C(=N1)Cl)F>>C(C1=CC=CC=C1)N1CCN(CC1)C1=CC=C(C=C1)NC1=NC(=NC=C1F)Cl | Cl[c:8]1[c:2]([F:1])[cH:3][n:4][c:5]([Cl:6])[n:7]1.[NH2:9][c:10]1[cH:11][cH:12][c:13]([N:14]2[CH2:15][CH2:16][N:17]([CH2:18][c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[CH2:25][CH2:26]2)[cH:27][cH:28]1>>[F:1][c:2]1[cH:3][n:4][c:5]([Cl:6])[n:7][c:8]1[NH:9][c:10]1[cH:11][cH:12][c:13]([N:14]2[CH2:15][CH2:16][N:17]([CH2:18... | Fc1cnc(Cl)nc1Cl.Nc1ccc(N2CCN(Cc3ccccc3)CC2)cc1 | Fc1cnc(Cl)nc1Nc1ccc(N2CCN(Cc3ccccc3)CC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CN2CCN(c3ccc(Nc4ccncn4)cc3)CC2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[F;D1;H0:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[Cl;D1;H0:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[F;D1;H0:8]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[#7;a:2]:1 | null | [] | null | null | null | null | In like manner to the preparation of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine, 4-(N-benzylpiperazino)aniline and 2,4-dichloro-5-fluoropyrimidine gave N4-[4-(N-benzylpiperazino)phenyl]-2-chloro-5-fluoro-4-pyrimidineamine. 1H NMR (CDCl3): δ 2.81 (m, 4H), 3.37 (m, 6H), 6.85 (br, 1H), 6.93 (d, J=9.0... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | HCl | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1ccc(N2CCN(Cc3ccccc3)CC2)cc1>>Fc1cnc(Cl)nc1Nc1ccc(N2CCN(Cc3ccccc3)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6a7fbcec461944efa5c16ea2a3ff0545 | Fc1cnc(Cl)nc1Cl.Nc1cccc(CO)c1>>OCc1cccc(Nc2nc(Cl)ncc2F)c1 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.ClC1=NC=C(C(=N1)Cl)F.NC=1C=C(CO)C=CC1>>ClC1=NC=C(C(=N1)NC1=CC(=CC=C1)CO)F | Cl[c:9]1[n:10][c:11]([Cl:12])[n:13][cH:14][c:15]1[F:16].[OH:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH2:8])[cH:17]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][c:11]([Cl:12])[n:13][cH:14][c:15]2[F:16])[cH:17]1 | Fc1cnc(Cl)nc1Cl.Nc1cccc(CO)c1 | OCc1cccc(Nc2nc(Cl)ncc2F)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[F;D1;H0:7]-[c:6]1:[c:5]:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | In a manner similar to the preparation of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine, 2,4-dichloro-5-fluoropyrimidine and 3-aminobenzylalcohol were reacted to yield 2-chloro-5-fluoro-N4-[3-(hydroxymethyl)phenyl]-4-pyrimidineamine. 1H NMR (CDCl3): δ 8.45 (bs, 1H), 7.96 (d, 1H, J=2.9 Hz), 7.65 (d, 1... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HCl | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1cccc(CO)c1>>OCc1cccc(Nc2nc(Cl)ncc2F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8fb91868364347f985b86776a2ca4f3d | Fc1cnc(Cl)nc1Cl.Nc1ccc(CO)cc1>>OCc1ccc(Nc2nc(Cl)ncc2F)cc1 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.ClC1=NC=C(C(=N1)Cl)F.NC1=CC=C(CO)C=C1>>ClC1=NC=C(C(=N1)NC1=CC=C(C=C1)CO)F | Cl[c:8]1[n:9][c:10]([Cl:11])[n:12][cH:13][c:14]1[F:15].[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:16][cH:17]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][c:10]([Cl:11])[n:12][cH:13][c:14]2[F:15])[cH:16][cH:17]1 | Fc1cnc(Cl)nc1Cl.Nc1ccc(CO)cc1 | OCc1ccc(Nc2nc(Cl)ncc2F)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[F;D1;H0:7]-[c:6]1:[c:5]:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | null | [] | null | null | null | null | In a manner similar to the preparation of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine, 2,4-dichloro-5-fluoropyrimidine and 4-aminobenzylalcohol were reacted to yield 2-chloro-5-fluoro-N4-[4-(hydroxymethyl)phenyl]-4-pyrimidineamine. 1H NMR (CDCl3): δ 8.08 (d, 1H, J=2.7 Hz), 7.62 (d, 2H, J=9.0 Hz), 7... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HCl | null | null | null | Fc1cnc(Cl)nc1Cl.Nc1ccc(CO)cc1>>OCc1ccc(Nc2nc(Cl)ncc2F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-264555ecfa7443aa8dbd1fe2c3f56e85 | CCOC(=O)CN.CCOC(=O)c1nc(Cl)nc(Cl)c1[N+](=O)[O-]>>CCOC(=O)CNc1nc(Cl)nc(C(=O)OCC)c1[N+](=O)[O-] | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.ClC1=NC(=C(C(=N1)Cl)[N+](=O)[O-])C(=O)OCC.Cl.C(C)OC(CN)=O>>C(C)OC(CNC1=NC(=NC(=C1[N+](=O)[O-])C(=O)OCC)Cl)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][NH2:7].Cl[c:8]1[n:9][c:10]([Cl:11])[n:12][c:13]([C:14](=[O:15])[O:16][CH2:17][CH3:18])[c:19]1[N+:20](=[O:21])[O-:22]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][NH:7][c:8]1[n:9][c:10]([Cl:11])[n:12][c:13]([C:14](=[O:15])[O:16][CH2:17][CH3:18])[c:19]1[N+:20](=[O:21])[O-:22] | CCOC(=O)CN.CCOC(=O)c1nc(Cl)nc(Cl)c1[N+](=O)[O-] | CCOC(=O)CNc1nc(Cl)nc(C(=O)OCC)c1[N+](=O)[O-] | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncnc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[C:6](-[#8:7])=[O;D1;H0:8]):[c:9]:1-[#7;+:10].[C:11]-[#8:12]-[C:13](=[O;D1;H0:14])-[C:15]-[NH2;D1;+0:16]>>[#7;+:10]-[c:9]1:[c:5](-[C:6](-[#8:7])=[O;D1;H0:8]):[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:16]-[C:15]-[C:13](=[O;D1;H0:14])-[#8:12]-[C:11] | null | [] | null | null | null | null | In a manner similar to the preparation of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine, 2,4-dichloro-6-ethoxycarbonyl-5-nitropyrimidine and glycine ethyl ester hydrochloride salt were reacted to yield N-(2-chloro-6-ethoxycarbonyl-5-nitro-4-pyrimidinyl)glycine Ethyl Ester. 1H NMR (CDCl3): δ 8.87 (bs,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1 | HCl | null | null | null | CCOC(=O)CN.CCOC(=O)c1nc(Cl)nc(Cl)c1[N+](=O)[O-]>>CCOC(=O)CNc1nc(Cl)nc(C(=O)OCC)c1[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1357eb418beb4d46a011fd3448643b01 | Fc1cnc(Cl)nc1Cl.NCC(O)c1ccccc1>>OC(CNc1nc(Cl)ncc1F)c1ccccc1 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.ClC1=NC=C(C(=N1)Cl)F.NCC(O)C1=CC=CC=C1>>ClC1=NC=C(C(=N1)NCC(C1=CC=CC=C1)O)F | Cl[c:5]1[n:6][c:7]([Cl:8])[n:9][cH:10][c:11]1[F:12].[OH:1][CH:2]([CH2:3][NH2:4])[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[OH:1][CH:2]([CH2:3][NH:4][c:5]1[n:6][c:7]([Cl:8])[n:9][cH:10][c:11]1[F:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | Fc1cnc(Cl)nc1Cl.NCC(O)c1ccccc1 | OC(CNc1nc(Cl)ncc1F)c1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CCNc2ccncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7].[C:8]-[C:9]-[NH2;D1;+0:10]>>[C:8]-[C:9]-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7] | null | [] | null | null | null | null | In a manner similar to the preparation of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine, 2,4-dichloro-5-fluoropyrimidine and 2-amino-1-phenylethanol were reacted to yield 2-chloro-5-fluoro-N4-(2-hydroxy-2-phenylethyl)-4-pyrimidineamine. 1H NMR (CDCl3): δ 7.88 (d, 1H, J=3.0 Hz), 7.41-7.32 (m, 5H), 5.7... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HCl | null | null | null | Fc1cnc(Cl)nc1Cl.NCC(O)c1ccccc1>>OC(CNc1nc(Cl)ncc1F)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c884a0178729442f84b7137249c4819d | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.NCc1ccco1>>Fc1cnc(Cl)nc1NCc1ccco1 | ClC1=NC=C(C(=N1)NC1=CC2=C(C=C1)OCCO2)F.ClC1=NC=C(C(=N1)Cl)F.C(C1=CC=CO1)N>>ClC1=NC=C(C(=N1)NCC1=CC=CO1)F | c1cc2c(cc1N[c:8]1[c:2]([F:1])[cH:3][n:4][c:5]([Cl:6])[n:7]1)OCCO2.[NH2:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][o:15]1>>[F:1][c:2]1[cH:3][n:4][c:5]([Cl:6])[n:7][c:8]1[NH:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][o:15]1 | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.NCc1ccco1 | Fc1cnc(Cl)nc1NCc1ccco1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 49fa1c8bcf8f8680bcf3c839aefa9cf12322d86ef58184c09a397108941f615c | a713e3fdd0c6b07745ba76404ca21e630fa98570823aec82a6b723a23739e7e7 | c1coc(CNc2ccncn2)c1 | [#8;a:1]:[c:2]-[C:3]-[NH2;D1;+0:4].[Cl;D1;H0:5]-[c:6]1:[#7;a:7]:[c:8]:[c:9](-[F;D1;H0:10]):[c;H0;D3;+0:11](-N-c2:c:c:c3:c(:c:2)-O-C-C-O-3):[#7;a:12]:1>>[#8;a:1]:[c:2]-[C:3]-[NH;D2;+0:4]-[c;H0;D3;+0:11]1:[#7;a:12]:[c:6](-[Cl;D1;H0:5]):[#7;a:7]:[c:8]:[c:9]:1-[F;D1;H0:10] | null | [] | null | null | null | null | In a manner similar to the preparation of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine, 2,4-dichloro-5-fluoropyrimidine and furfurylamine were reacted to yield 2-chloro-5-fluoro-N4-(furfuryl)-4-pyrimidineamine. 1H NMR (CDCl3): δ 7.91 (d, 1H, J=1.8 Hz), 7.39 (d, 1H, J=1.2 Hz), 6.35 (m, 2H), 5.50 (bs,... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary amine.Secondary amine | Secondary amine | c1cncnc1.c1ccc2c(c1)OCCO2 | c1cncnc1 | c1cncnc1.c1ccoc1 | HO- | null | null | null | Fc1cnc(Cl)nc1Nc1ccc2c(c1)OCCO2.NCc1ccco1>>Fc1cnc(Cl)nc1NCc1ccco1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ad7614da9b3f49ee912dfe6655f7a641 | CC(N)c1ccc(O)cc1.Fc1cnc(Cl)nc1Cl>>CC(Nc1nc(Cl)ncc1F)c1ccc(O)cc1 | ClC1=NC=C(C(=N1)Cl)F.OC1=CC=C(C=C1)C(C)N>>ClC1=NC=C(C(=N1)NC(C)C1=CC=C(C=C1)O)F | [CH3:1][CH:2]([NH2:3])[c:12]1[cH:13][cH:14][c:15]([OH:16])[cH:17][cH:18]1.Cl[c:4]1[n:5][c:6]([Cl:7])[n:8][cH:9][c:10]1[F:11]>>[CH3:1][CH:2]([NH:3][c:4]1[n:5][c:6]([Cl:7])[n:8][cH:9][c:10]1[F:11])[c:12]1[cH:13][cH:14][c:15]([OH:16])[cH:17][cH:18]1 | CC(N)c1ccc(O)cc1.Fc1cnc(Cl)nc1Cl | CC(Nc1nc(Cl)ncc1F)c1ccc(O)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7].[C;D1;H3:8]-[C:9](-[NH2;D1;+0:10])-[c:11]>>[C;D1;H3:8]-[C:9](-[c:11])-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7] | null | [] | null | null | null | null | In like manner to the preparation of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine, 2,4-dichloro-5-fluoropyrimidine was reacted with 1-(4-hydroxyphenyl)ethylamine to provide (±)-2-chloro-5-fluoro-N4-[1-(4-hydroxyphenyl)ethyl]-4-pyrimidineamine. 1H NMR (CDCl3): δ 7.88 (d, 1H, J=2.3 Hz), 7.50-7.47 (dd,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HCl | null | null | null | CC(N)c1ccc(O)cc1.Fc1cnc(Cl)nc1Cl>>CC(Nc1nc(Cl)ncc1F)c1ccc(O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7eb2335acb3241b4ba7b699c3da9b141 | CC(N)c1ccc(Br)cc1.Fc1cnc(Cl)nc1Cl>>CC(Nc1nc(Cl)ncc1F)c1ccc(Br)cc1 | ClC1=NC=C(C(=N1)Cl)F.BrC1=CC=C(C=C1)C(C)N>>BrC1=CC=C(C=C1)C(C)NC1=NC(=NC=C1F)Cl | [CH3:1][CH:2]([NH2:3])[c:12]1[cH:13][cH:14][c:15]([Br:16])[cH:17][cH:18]1.Cl[c:4]1[n:5][c:6]([Cl:7])[n:8][cH:9][c:10]1[F:11]>>[CH3:1][CH:2]([NH:3][c:4]1[n:5][c:6]([Cl:7])[n:8][cH:9][c:10]1[F:11])[c:12]1[cH:13][cH:14][c:15]([Br:16])[cH:17][cH:18]1 | CC(N)c1ccc(Br)cc1.Fc1cnc(Cl)nc1Cl | CC(Nc1nc(Cl)ncc1F)c1ccc(Br)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7].[C;D1;H3:8]-[C:9](-[NH2;D1;+0:10])-[c:11]>>[C;D1;H3:8]-[C:9](-[c:11])-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7] | null | [] | null | null | null | null | In like manner to the preparation of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine, 2,4-dichloro-5-fluoropyrimidine was reacted with 1-(4-bromophenyl)ethylamine to provide (±)-N4-[1-(4-bromophenyl)ethyl]-2-chloro-5-fluoro-4-pyrimidineamine: 1H NMR (CDCl3): δ 7.88 (d, 1H, J=2.3 Hz), 7.49 (d, 2H, J=8.7... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HCl | null | null | null | CC(N)c1ccc(Br)cc1.Fc1cnc(Cl)nc1Cl>>CC(Nc1nc(Cl)ncc1F)c1ccc(Br)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8e75d8280b654e80b2d52046fbfbe3c8 | Fc1cnc(Cl)nc1Cl.NC(c1cc(C(F)(F)F)cc(C(F)(F)F)c1)c1cc(C(F)(F)F)cc(C(F)(F)F)c1>>Fc1cnc(Cl)nc1NC(c1cc(C(F)(F)F)cc(C(F)(F)F)c1)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 | ClC1=NC=C(C(=N1)Cl)F.FC(C=1C=C(C=C(C1)C(F)(F)F)C(C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)N)(F)F>>ClC1=NC=C(C(=N1)NC(C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)F | Cl[c:8]1[c:2]([F:1])[cH:3][n:4][c:5]([Cl:6])[n:7]1.[NH2:9][CH:10]([c:11]1[cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][c:19]([C:20]([F:21])([F:22])[F:23])[cH:24]1)[c:25]1[cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32][c:33]([C:34]([F:35])([F:36])[F:37])[cH:38]1>>[F:1][c:2]1[cH:3][n:4][c:5]([Cl:6])[n:7][c:8]1[NH... | Fc1cnc(Cl)nc1Cl.NC(c1cc(C(F)(F)F)cc(C(F)(F)F)c1)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 | Fc1cnc(Cl)nc1NC(c1cc(C(F)(F)F)cc(C(F)(F)F)c1)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(C(Nc2ccncn2)c2ccccc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[F;D1;H0:8].[NH2;D1;+0:9]-[C:10](-[c:11])-[c:12]>>[Cl;D1;H0:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[F;D1;H0:8]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:10](-[c:11])-[c:12]):[#7;a:2]:1 | null | [] | null | null | null | null | In like manner to the preparation of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro-4-pyrimidineamine, 2,4-dichloro-5-fluoropyrimidine was reacted with di[3,5-di(trifluoromethyl)phenyl]methylamine to provide 2-chloro-N4-[[di(3,5-di(trifluoromethyl)phenyl)]methyl]-5-fluoro-4-pyrimidineamine. 1H NMR (CDCl3): δ 8.06 (d, 1... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1.c1ccccc1 | HCl | null | null | null | Fc1cnc(Cl)nc1Cl.NC(c1cc(C(F)(F)F)cc(C(F)(F)F)c1)c1cc(C(F)(F)F)cc(C(F)(F)F)c1>>Fc1cnc(Cl)nc1NC(c1cc(C(F)(F)F)cc(C(F)(F)F)c1)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4e89bcc4f5ab4b429e89918af8b6e3cd | Fc1cnc(Cl)nc1Cl.NC1c2ccccc2-c2ccccc21>>Fc1cnc(Cl)nc1NC1c2ccccc2-c2ccccc21 | Cl.NC1C2=CC=CC=C2C=2C=CC=CC12.ClC1=NC=C(C(=N1)Cl)F.C(C)(C)N(CC)C(C)C>>ClC1=NC=C(C(=N1)NC1C2=CC=CC=C2C=2C=CC=CC12)F | Cl[c:8]1[c:2]([F:1])[cH:3][n:4][c:5]([Cl:6])[n:7]1.[NH2:9][CH:10]1[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2-[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]21>>[F:1][c:2]1[cH:3][n:4][c:5]([Cl:6])[n:7][c:8]1[NH:9][CH:10]1[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2-[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]21 | Fc1cnc(Cl)nc1Cl.NC1c2ccccc2-c2ccccc21 | Fc1cnc(Cl)nc1NC1c2ccccc2-c2ccccc21 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc2c(c1)-c1ccccc1C2Nc1ccncn1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1-[F;D1;H0:8].[NH2;D1;+0:9]-[C:10](-[c:11])-[c:12]>>[Cl;D1;H0:4]-[c:3]1:[#7;a:5]:[c:6]:[c:7](-[F;D1;H0:8]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:10](-[c:11])-[c:12]):[#7;a:2]:1 | null | [] | null | null | null | null | In like manner to the preparation of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro 4-pyrimidineamine, 9-aminofluorene hydrochloride and 2,4-dichloro-5-fluoropyrimidine with added diisopropylethylamine were reacted to produce 2-chloro-N-(fluoren-9-yl)-5-fluoro-4-pyrimidineamine. 1H NMR (CDCl3): δ 7.97 (d, 1H, J=2.3 Hz)... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccc2c(c1)Cc1ccccc12 | HCl | null | null | null | Fc1cnc(Cl)nc1Cl.NC1c2ccccc2-c2ccccc21>>Fc1cnc(Cl)nc1NC1c2ccccc2-c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d1a94529afb748ada453c625063efeef | CC(N)c1ccc(F)cc1.Fc1cnc(Cl)nc1Cl>>CC(Nc1nc(Cl)ncc1F)c1ccc(F)cc1 | FC1=CC=C(C(C)N)C=C1.ClC1=NC=C(C(=N1)Cl)F>>ClC1=NC=C(C(=N1)NC(C)C1=CC=C(C=C1)F)F | [CH3:1][CH:2]([NH2:3])[c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1.Cl[c:4]1[n:5][c:6]([Cl:7])[n:8][cH:9][c:10]1[F:11]>>[CH3:1][CH:2]([NH:3][c:4]1[n:5][c:6]([Cl:7])[n:8][cH:9][c:10]1[F:11])[c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1 | CC(N)c1ccc(F)cc1.Fc1cnc(Cl)nc1Cl | CC(Nc1nc(Cl)ncc1F)c1ccc(F)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7].[C;D1;H3:8]-[C:9](-[NH2;D1;+0:10])-[c:11]>>[C;D1;H3:8]-[C:9](-[c:11])-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7] | null | [] | null | null | null | null | In like manner to the preparation of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro 4-pyrimidineamine, 4-fluoro-α-methylbenzylamine and 2,4-dichloro-5-fluoropyrimidine were reacted to produce (±)-N-(2-chloro-5-fluoropyrimidinyl)-1-(4-fluorophenyl)ethylamine. 1H NMR (CDCl3): δ 7.87 (d, 1H, J=2.3 Hz), 7.37-7.33 (dd, 2H, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HCl | null | null | null | CC(N)c1ccc(F)cc1.Fc1cnc(Cl)nc1Cl>>CC(Nc1nc(Cl)ncc1F)c1ccc(F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8d22a94b8431459fa2dabc0aae5f5505 | COC(=O)c1cc(N)cn1C.Clc1ncc(Br)c(Cl)n1>>COC(=O)c1cc(Nc2nc(Cl)ncc2Br)cn1C | BrC=1C(=NC(=NC1)Cl)Cl.Cl.CN1C(=CC(=C1)N)C(=O)OC.C(C)(C)N(CC)C(C)C>>BrC=1C(=NC(=NC1)Cl)NC=1C=C(N(C1)C)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH2:8])[cH:17][n:18]1[CH3:19].Cl[c:9]1[n:10][c:11]([Cl:12])[n:13][cH:14][c:15]1[Br:16]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH:8][c:9]2[n:10][c:11]([Cl:12])[n:13][cH:14][c:15]2[Br:16])[cH:17][n:18]1[CH3:19] | COC(=O)c1cc(N)cn1C.Clc1ncc(Br)c(Cl)n1 | COC(=O)c1cc(Nc2nc(Cl)ncc2Br)cn1C | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2cc[nH]c2)ncn1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[Br;D1;H0:7].[#8:8]-[C:9](=[O;D1;H0:10])-[c:11]1:[c:12]:[c:13](-[NH2;D1;+0:14]):[c:15]:[#7;a:16]:1-[C;D1;H3:17]>>[#8:8]-[C:9](=[O;D1;H0:10])-[c:11]1:[c:12]:[c:13](-[NH;D2;+0:14]-[c;H0;D3;+0:1]2:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:2-[Br;D1;H0:7]):[c:15]:[#7;a:16]:... | null | [] | null | null | null | null | In like manner to the preparation of 2-chloro-N4-(3,4-ethylenedioxyphenyl)-5-fluoro 4-pyrimidineamine, 5-bromo-2,4-dichloropyrimidine and N-methyl-2-carbomethoxy-4-aminopyrrole hydrochloride with added diisopropylethylamine were reacted to produce the desired product 5-bromo-2-chloro-N-(N-methyl-2-carbomethoxypyrrol-4-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cc[nH]c1.c1cncnc1 | HCl | null | null | null | COC(=O)c1cc(N)cn1C.Clc1ncc(Br)c(Cl)n1>>COC(=O)c1cc(Nc2nc(Cl)ncc2Br)cn1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a5568ffec01a4a99993d705f5da73028 | CCCCOc1ccc(N)cc1.Fc1cnc(Cl)nc1Cl>>CCCCOc1ccc(Nc2nc(Cl)ncc2F)cc1 | [OH-].[Na+].ClC1=NC=C(C(=N1)Cl)F.C(CCC)OC1=CC=C(N)C=C1.Cl>>ClC1=NC=C(C(=N1)NC1=CC=C(C=C1)OCCCC)F | [CH3:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([NH2:10])[cH:19][cH:20]1.Cl[c:11]1[n:12][c:13]([Cl:14])[n:15][cH:16][c:17]1[F:18]>>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([NH:10][c:11]2[n:12][c:13]([Cl:14])[n:15][cH:16][c:17]2[F:18])[cH:19][cH:20]1 | CCCCOc1ccc(N)cc1.Fc1cnc(Cl)nc1Cl | CCCCOc1ccc(Nc2nc(Cl)ncc2F)cc1 | null | null | CC(=O)C.O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[F;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[F;D1;H0:7]-[c:6]1:[c:5]:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 80 | [{"value": 80.0, "product": "ClC1=NC=C(C(=N1)NC1=CC=C(C=C1)OCCCC)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.0, "product": "ClC1=NC=C(C(=N1)NC1=CC=C(C=C1)OCCCC)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2,4-dichloro-5-fluoropyrimidine (0.5 g, 3.0 mmol) and 4-n-butoxyaniline (0.49 g, 3 mmol) in acetone/H2O (1:9 mL) at room temperature was added concentrated HCl (0.1 mL). The mixture was heated at reflux for 1 h, cooled to room temperature, and made basic with 2 N NaOH (2 mL). The aqueous layer was extr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HCl | CC(=O)C.O | null | null | CCCCOc1ccc(N)cc1.Fc1cnc(Cl)nc1Cl>CC(=O)C.O>CCCCOc1ccc(Nc2nc(Cl)ncc2F)cc1 |
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