original_index int64 2 1.77M | extracted_from_file stringclasses 489
values | date_of_experiment timestamp[ns]date | grant_date timestamp[ns]date 1976-01-01 00:01:00 2016-01-01 00:09:00 | is_mapped bool 1
class | rxn_str stringlengths 87 6.12k | reactant_000 stringlengths 1 902 | reactant_001 stringlengths 1 902 ⌀ | reactant_002 null | agent_000 stringlengths 1 540 ⌀ | agent_001 stringlengths 1 852 ⌀ | agent_002 stringlengths 1 247 ⌀ | agent_003 null | agent_004 null | agent_005 null | agent_006 null | agent_007 null | agent_008 null | agent_009 null | agent_010 null | agent_011 null | agent_012 null | agent_013 null | agent_014 null | agent_015 null | agent_016 null | solvent_000 stringclasses 446
values | solvent_001 stringclasses 405
values | solvent_002 null | solvent_003 null | solvent_004 null | solvent_005 null | solvent_006 null | solvent_007 null | solvent_008 null | solvent_009 null | solvent_010 null | temperature float64 -230 30.1k ⌀ | rxn_time float64 0 2.16k ⌀ | procedure_details stringlengths 8 24.5k | product_000 stringlengths 1 484 | product_001 null | yield_000 float64 0 90,205,156,600B ⌀ | yield_001 float64 0 100M ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1,074,444 | ord_dataset-5df93261afc143c3ae919a57ff4fc1d4 | null | 2011-01-01T00:07:00 | true | [NH2:1][C:2]1[S:13][C:5]2[C:6]([CH3:12])([CH3:11])[O:7][C:8]([CH3:10])([CH3:9])[C:4]=2[C:3]=1[C:14]([O:16][CH2:17][CH2:18][CH3:19])=[O:15].[F:20][C:21]([F:32])([F:31])[C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24](Cl)=[O:25]>>[CH3:10][C:8]1([CH3:9])[O:7][C:6]([CH3:11])([CH3:12])[C:5]2[S:13][C:2]([NH:1][C:24](=[O:2... | CCCOC(=O)c1c(N)sc2c1C(C)(C)OC2(C)C | O=C(Cl)c1ccccc1C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from the product of Example 62A and commercially available 2-trifluoromethylbenzoyl chloride using the procedure described for Example 1B. 1H NMR (DMSO-d6, 300 MHz) δ 0.90 (t, J=7.5 Hz, 3H), 1.50 (s, 6H), 1.54 (s, 6H), 1.63-1.75 (m, 2H), 4.22 (t, J=6.8 Hz, 2H), 7.79-7.95 (m, 4H), 11.47 (... | CCCOC(=O)c1c(NC(=O)c2ccccc2C(F)(F)F)sc2c1C(C)(C)OC2(C)C | null | null | null |
931,658 | ord_dataset-d8a5dc784dde4465894ec7c69d2e3ba6 | null | 2010-01-01T00:01:00 | true | [Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5](/[CH:10]=[CH:11]/[C:12]([OH:14])=O)=[C:4]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:3]=1.[F:20][C:21]1[CH:35]=[CH:34][C:24]([CH2:25][N:26]2[CH2:31][C@H:30]([CH3:32])[NH:29][CH2:28][C@H:27]2[CH3:33])=[CH:23][CH:22]=1.CCN=C=NCCCN(C)C.Cl.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[Cl:1]... | COc1cc(/C=C/C(=O)O)c(NS(C)(=O)=O)cc1Cl | C[C@@H]1CN[C@@H](C)CN1Cc1ccc(F)cc1 | null | CCN=C=NCCCN(C)C | Cl | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | (E)-3-(4-Chloro-2-methanesulfonylamino-5-methoxyphenyl)-acrylic acid (100 mg; 0.32 mmol), (2R,5S)-1-(4-fluorobenzyl)-2,5-dimethylpiperazine (Mavunkel, Babu J. et al., WO 00171535) (73 mg; 0.32 mmol) and EDCl.HCl (75 mg, 0.39 mmol), HOBt (5 mg; 0.03 mmol) were dissolved in DMF (2 ml) and stirred over night. The reaction... | COc1cc(/C=C/C(=O)N2C[C@H](C)N(Cc3ccc(F)cc3)C[C@H]2C)c(NS(C)(=O)=O)cc1Cl | null | 82.7 | null |
1,571,698 | ord_dataset-9741bb5fd93044078df2a45f45733054 | null | 2015-01-01T00:04:00 | true | [CH2:1]([O:8][C:9](=[O:24])[NH:10][C@H:11]([CH:21]([CH3:23])[CH3:22])[C:12]([NH:14][CH2:15][CH:16](OC)OC)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.O.C([O-])([O-])=O.[Na+].[Na+]>>[CH:21]([C@@H:11]1[C:12](=[O:13])[NH:14][CH:15]=[CH:16][N:10]1[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]... | COC(CNC(=O)[C@H](NC(=O)OCc1ccccc1)C(C)C)OC | null | null | O=C([O-])[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | 25 | 12 | (R)-benzyl(1-((2,2-dimethoxyethyl)amino)-3-methyl-1-oxobutan-2-yl)carbamate (335 g, 0.99 mol) was added in portions to a cooled TFA-H2O (temperature <5° C., VTFA/VH2O=7/3, 2 L), and the solution was stirred at rt for 12 h. The solution was added slowly into stirring cooled sat. aq. Na2CO3 (2.5 L) to keep the pH>8. The ... | CC(C)[C@@H]1C(=O)NC=CN1C(=O)OCc1ccccc1 | null | 95.4 | null |
1,550,177 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [F:1][CH2:2][C:3]1([S:6]([NH:9][C:10]([C@@:12]2([NH:17]C(=O)OC(C)(C)C)[CH2:14][C@H:13]2[CH:15]=[CH2:16])=[O:11])(=[O:8])=[O:7])[CH2:5][CH2:4]1.[ClH:25]>O1CCOCC1>[ClH:25].[NH2:17][C@:12]1([C:10]([NH:9][S:6]([C:3]2([CH2:2][F:1])[CH2:5][CH2:4]2)(=[O:8])=[O:7])=[O:11])[CH2:14][C@H:13]1[CH:15]=[CH2:16] | C=C[C@@H]1C[C@]1(NC(=O)OC(C)(C)C)C(=O)NS(=O)(=O)C1(CF)CC1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | null | A solution of tert-butyl (1R,2S)-1-(1-(fluoromethyl)cyclopropylsulfonylcarbamoyl)-2-vinylcyclopropylcarbamate (11.5 g, 31.7 mmol) in 4 N HCl in dioxane (100 mL) was stirred at room temperature for 1 h. The solvent was evaporated under reduced pressure and the residue was washed with diethyl ether to get crude compound ... | C=C[C@@H]1C[C@]1(N)C(=O)NS(=O)(=O)C1(CF)CC1 | null | 72 | null |
251,939 | ord_dataset-49bd993346b64eeeb2a8fe2643164a0a | null | 1992-01-01T00:08:00 | true | [C:1]([O:4][C:5]1[C:6]([CH3:21])=[C:7]([CH3:20])[C:8]2[O:13][C:12]([CH2:15][CH2:16]Br)([CH3:14])[CH2:11][CH2:10][C:9]=2[C:18]=1[CH3:19])(=[O:3])[CH3:2].[CH3:22][NH:23][CH3:24].O>CN(C)C=O>[C:1]([O:4][C:5]1[C:6]([CH3:21])=[C:7]([CH3:20])[C:8]2[O:13][C:12]([CH2:15][CH2:16][N:23]([CH3:24])[CH3:22])([CH3:14])[CH2:11][CH2:10... | CC(=O)Oc1c(C)c(C)c2c(c1C)CCC(C)(CCBr)O2 | CNC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 40 | A mixture of 3.55 g (0.01 mol) of 3,4-dihydro-2-(2- bromoethyl)-2,5,7,8-tetramethyl-2H-benzopyran-6-yl acetate and 2.0 g of liquid dimethylamine in 50 ml of dimethylformamide is stirred at room temperature for 40 hours. Water is added and the product is extracted with ethyl acetate and ethyl ether. The extract is washe... | CC(=O)Oc1c(C)c(C)c2c(c1C)CCC(C)(CCN(C)C)O2 | null | null | null |
1,683,211 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:19][CH2:18][C:17]3[C:16]4[CH2:15][C:14]([CH3:21])([CH3:20])[CH2:13][C:12]=4[S:11][C:10]=3[C:9]2=[O:22])[C:3]=1[CH:23]=[O:24].[CH3:25][O:26][CH2:27][CH2:28][N:29]1[CH2:34][CH2:33][N:32]2[N:35]=[C:36]([NH:38][C:39]3[C:40](=[O:55])[N:41]([CH3:54])[CH:42]=[C:43](B4OC(C)(C)C(C)(C)... | COCCN1CCn2nc(Nc3cc(B4OC(C)(C)C(C)(C)O4)cn(C)c3=O)cc2C1 | CC1(C)Cc2sc3c(c2C1)CCN(c1nccc(Cl)c1C=O)C3=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following the procedure in Example 304, and starting with 4-chloro-2-{4,4-dimethyl-9-oxo-7-thia-10-azatricyclo[6.4.0.02,6]dodeca-1(8),2(6)-dien-10-yl}pyridine-3-carbaldehyde 109a (250 mg, 0.693 mmol) and 3-(5-(2-methoxyethyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamino)-1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-diox... | COCCN1CCn2nc(Nc3cc(-c4ccnc(N5CCc6c(sc7c6CC(C)(C)C7)C5=O)c4C=O)cn(C)c3=O)cc2C1 | null | null | null |
1,147,112 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | CCN(C(C)C)C(C)C.[Br:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH2:14]Br.[CH3:19][NH:20][CH2:21][CH2:22][C:23]#[N:24]>CN(C=O)C>[Br:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH2:14][N:20]([CH3:19])[CH2:21][CH2:22][C:23]#[N:24] | CNCCC#N | BrCc1cccc(Br)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | 16 | Hunig's base (26.5 mL, 0.15 mol) was added to 3-bromobenzyl bromide (38 g, 0.15 mol) and N-methyl-β-alanine nitrile (14.2 mL, 0.15 mol) in dry DMF (400 mL). The solution was stirred 16 h, concentrated in vacuo to near dryness, triturated with ether/EtOAc, and filtered. [A second reaction was repeated on 12 g]. The comb... | CN(CCC#N)Cc1cccc(Br)c1 | null | 116.9 | null |
1,159,360 | ord_dataset-b195433d5c354ddfb6cde0d53c41910f | null | 2012-01-01T00:04:00 | true | [CH2:1]([C:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][C:13]([Cl:19])=[CH:14][CH:15]=2)[N:10]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([N:26]3C(C)=CC=C3C)[N:21]=2)[C:9]=1[C:33]1[O:34][CH:35]=[CH:36][N:37]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.NO>CCO.O>[NH2:26][C:22]1[N:21]=[C:20]([N:10]2[C:11]3[C:16](=[CH:15][CH:14]=[... | Cc1ccc(C)n1-c1cccc(-n2c(-c3ncco3)c(Cc3ccccc3)c(=O)c3ccc(Cl)cc32)n1 | null | null | Cl | NO | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | null | null | A solution of 3-benzyl-7-chloro-1-[6-(2,5-dimethyl-pyrrol-1-yl)-pyridin-2-yl]-2-oxazol-2-yl-1H-quinolin-4-one (640 mg) in EtOH (3.5 mL) and water (1.3 mL) and hydroxylamine hydrochloride (450 mg) was stirred for 48 h at 60° C. After evaporation of volatiles, the dark brown residue was partitioned into EtOAc and H2O, an... | Nc1cccc(-n2c(-c3ncco3)c(Cc3ccccc3)c(=O)c3ccc(Cl)cc32)n1 | null | null | null |
1,127,533 | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | null | 2012-01-01T00:01:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:22])[C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[N:12][CH:11]=2)=[CH:4][C:3]=1[NH:23][C:24](=[O:32])[C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1.[C:33](Cl)(=[O:38])[CH2:34][CH:35]([CH3:37])[CH3:36]>>[CH3:36][CH:35]([CH3:37])[CH2:3... | O=C(Nc1ccc(Cl)c(NC(=O)c2ccc(F)cc2)c1)c1ccc(N2CCNCC2)nc1 | CC(C)CC(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | N-(4-chloro-3-(4-fluorobenzamido)phenyl)-6-(piperazin-1-yl)nicotinamide (0.182 mmol) was used in general procedure 1 with isovaleryl chloride (0.20 mmol). The product was purified by RP-HPLC to give 6-(4-(3-methylbutanoyl)piperazin-1-yl)-N-(3-(4-fluorobenzamido)-4-chlorophenyl)-pyridine-3-carboxamide. MS (Q1) 538.5 (M)... | CC(C)CC(=O)N1CCN(c2ccc(C(=O)Nc3ccc(Cl)c(NC(=O)c4ccc(F)cc4)c3)cn2)CC1 | null | null | null |
806,642 | ord_dataset-da49b0378abf41bf92ab8ecdd3feb28b | null | 2008-01-01T00:02:00 | true | C([O:3][C:4](=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17](Br)[N:16]=2)=[O:14])[CH:7]=1)C.[Cl:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[C:28]([Cl:30])[CH:29]=1>>[Cl:23][C:24]1[CH:25]=[C:26]([C:17]2[N:16]=[C:15]([C:13]([NH:12][C:8]3[CH:7]=[C:6]([CH2:5][C:4]([OH:3])=[O:... | CCOC(=O)Cc1cccc(NC(=O)c2cccc(Br)n2)c1 | OB(O)c1cc(Cl)cc(Cl)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The pyridyl bromide (77)(44 mg, 0.12 mmol) was coupled to 3,5-dichloro-phenylboronic acid (20 mg, 0.10 mmol) using Method E. During this reaction, hydrolysis occurred. The residue was extracted using Work-up E1 to give the acid. The solid was further purified by preparative HPLC to give the title compound. | O=C(O)Cc1cccc(NC(=O)c2cccc(-c3cc(Cl)cc(Cl)c3)n2)c1 | null | null | null |
533,291 | ord_dataset-b1a34bc8c1204d51a772ed27396c794e | null | 2002-01-01T00:02:00 | true | [NH2:1][CH2:2][C:3]1[N:4]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([CH2:15][O:16][C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:26]=3[N:25]=[C:24]([CH3:27])[CH:23]=[CH:22]4)[C:9]=2[Cl:28])[CH:5]=[CH:6][CH:7]=1.[CH3:29][N:30]([CH3:44])[C:31]([C:33]1[CH:43]=[CH:42][C:36]([CH:37]=[CH:38][C:39](O)=[O:40])=[CH:35][CH:34]=1)=[O:... | CN(C)C(=O)c1ccc(C=CC(=O)O)cc1 | Cc1ccc2cccc(OCc3c(Cl)ccc(-n4cccc4CN)c3Cl)c2n1 | null | CCN=C=NCCCN(C)C | Cl | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | O | null | null | null | null | null | null | null | null | null | null | 18 | To a solution of 2-aminomethyl-1-[2,4-dichloro-3-(2-methylquinolin-8-yloxymethyl)phenyl]pyrrole (100 mg) and 4-(dimethylcarbamoyl)cinnamic acid (58.5 mg) in N,N-dimethylformamide (2 ml) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (55.8 mg) and 1-hydroxybenzotriazole (49.2 mg) at ambient tempe... | Cc1ccc2cccc(OCc3c(Cl)ccc(-n4cccc4CNC(=O)C=Cc4ccc(C(=O)N(C)C)cc4)c3Cl)c2n1 | null | 82 | null |
262,645 | ord_dataset-ddb1b60bec5c45e9a2938b6dac04376c | null | 1993-01-01T00:02:00 | true | BrC[CH2:3][C:4]([C:6]1[C:11]([CH3:12])=[CH:10][C:9]([CH3:13])=[CH:8][C:7]=1[CH3:14])=O.[NH2:15][C:16]([NH2:18])=[S:17]>CO>[NH2:18][C:16]1[S:17][CH:3]=[C:4]([C:6]2[C:11]([CH3:12])=[CH:10][C:9]([CH3:13])=[CH:8][C:7]=2[CH3:14])[N:15]=1 | Cc1cc(C)c(C(=O)CCBr)c(C)c1 | NC(N)=S | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 80 g of 2,4,6-trimethylphenyl bromoethyl ketone and 35 g of thiourea in 250 ml of methanol is refluxed for 3 hours. After cooling the reaction mixture, the precipitate is filtered off and washed abundantly with diethyl ether. After concentration of the filtrate to a third of the initial volume, a second b... | Cc1cc(C)c(-c2csc(N)n2)c(C)c1 | null | 70 | null |
561,013 | ord_dataset-7c28974b7fcf4c9c86d5f2a42ba328a2 | null | 2002-01-01T00:09:00 | true | [SH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13].[C:15]1([CH:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>FC(F)(F)C(O)=O>[C:15]1([CH:21]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[S:1][CH2:2][CH2:3][CH2:4][CH2:5][CH... | O=C(O)CCCCCCCCCCS | OC(c1ccccc1)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 11-mercaptoundecanoic acid (300 mg, 1.3 mmol) and diphenylmethanol (255 mg, 1.3 mmol) in trifluoroacetic acid was stirred at RT, under nitrogen for 30 min. Trifluoroacetic acid was evaporated under high vacuum, the residue dissolved in ether (20 ml), washed with water (3×20 ml), dried and evaporated. The ... | O=C(O)CCCCCCCCCCSC(c1ccccc1)c1ccccc1 | null | 44 | null |
1,674,613 | ord_dataset-9cc455db05a444779921f786a45b21a6 | null | 2015-01-01T00:12:00 | true | Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH2:11][CH2:12][CH2:13][NH:14][CH2:15][CH:16]=2)=[CH:6][CH:5]=1.[H][H]>[Pd].CO>[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]2[CH2:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16]2)=[CH:8][CH:9]=1 | [H][H] | COc1ccc(C2=CCNCCC2)cc1 | null | [Pd] | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 5-(4-methoxyphenyl)-2,3,4,7-tetrahydro-1H-azepine hydrochloride (0.35 g, 1.5 mmol) and 10% palladium on carbon (0.2 g) in methanol (10 mL) was stirred overnight under balloon pressure of hydrogen. The reaction mixture was filtered through Celite and concentrated to yield 4-(4-methoxyphenyl)azepane (0.26 g,... | COc1ccc(C2CCCNCC2)cc1 | null | 80 | null |
740,624 | ord_dataset-437aa6654d5044ddaef3346dc4c6e08a | null | 2006-01-01T00:11:00 | true | [C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([NH:12][CH2:13][CH2:14][C:15]([O:17]CC)=[O:16])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([NH:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3] | CCOC(=O)CCNC(=O)CNC(=O)OC(C)(C)C | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 1.5 | A solution of (6) at 0° C. (3.43 g; 0.012 mmol) in methanol (40 ml) was treated with 2N sodium hydroxide (6.9 ml; 0.013 mmol). The mixture was stirred at ambient temperature for 90 minutes. After evaporation of the methanol and removal of the insoluble material by filtration, the solution was adjusted to pH5 with 6N hy... | CC(C)(C)OC(=O)NCC(=O)NCCC(=O)O | null | 16 | null |
1,679,625 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [C:1]([O:5][C:6](=[O:27])[N:7]([CH2:24]C=C)[CH2:8][C@@H:9]([N:21]=[N+:22]=[N-:23])[C@H:10]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:11]=[CH2:12])([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl.[Cl-].[Cl-].[Zn+2]>[C:1]([O:5][C:6]([N:7]1[CH2:24][CH:12]=[CH:11][C@@H:10]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18... | C=CCN(C[C@@H](N=[N+]=[N-])[C@@H](C=C)OCc1ccccc1)C(=O)OC(C)(C)C | null | null | [Cl-] | [Zn+2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | A solution of Mo(CHCMe2Ph)(NAr)(OCMe(CF3)2)2(phen) (8 mg, 9 μmol, 5 mol %) and ZnCl2 (1.2 mg, 9 μmol) in CH2Cl2 (18 mL) was heated for 30 min to 100° C. Subsequently, (2R,3R)-allyl-(2-azido-3-benzyloxy-pent-4-enyl)-carbamic acid tert-butylester (66 mg, 0.177 mmol) was added and the mixture was heated for 30 min under r... | CC(C)(C)OC(=O)N1CC=C[C@@H](OCc2ccccc2)[C@H](N=[N+]=[N-])C1 | null | null | null |
1,037,545 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:3]=[C:4](/[C:12](=[N:16]\[O:17][CH2:18][CH:19]([CH3:21])[CH3:20])/[C:13]([OH:15])=O)[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].[NH2:22][C:23]1[S:24][C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[N:27]=1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[S:24]1[C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[N:27]=[C:23]1[N... | Nc1nc2ccccc2s1 | CC(C)CO/N=C(/C(=O)O)c1ccc(S(C)(=O)=O)c(Cl)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | ClCCl | null | null | null | null | null | null | null | null | null | null | 2 | (E)-(3-chloro-4-methanesulfonyl-phenyl)-isobutoxyimino-acetic acid (prepared as in Example 24, 104 mg, 0.31 mmol), 2-aminobenzothiazole (47 mg, 0.31 mmol) and N,N-diisopropylethylamine (163 μL, 0.94 mmol) were combined in methylene chloride (1.5 mL) and cooled in an ice bath. O-(7-Azabenzotriazole-1-yl)-N,N,N′N′-tetram... | CC(C)CO/N=C(/C(=O)Nc1nc2ccccc2s1)c1ccc(S(C)(=O)=O)c(Cl)c1 | null | 59.5 | null |
353,838 | ord_dataset-930bf31b476c482e8ba87824089eb600 | null | 1997-01-01T00:02:00 | true | [F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[S:15])[NH:10][CH2:11][C:12](N)=[O:13])=[CH:4][CH:3]=1.[CH2:16](I)[CH3:17]>C(O)C>[CH2:16]([S:15][C:9]1[N:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[C:12](=[O:13])[CH2:11][N:10]=1)[CH3:17] | NC(=O)CNC(=S)Nc1ccc(F)cc1 | CCI | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 2-[3-(4-fluorophenyl)-thioureido]-acetamide (9.1 g) and ethyl iodide (12.5 g) was heated at reflux in ethanol (200 mL) for 4 hours. The solvent was evaporated. The residue was dissolved in ethyl acetate (500 mL) then washed with water. The organic phase was extracted with 2N HCl (2×400 mL). The acid extrac... | CCSC1=NCC(=O)N1c1ccc(F)cc1 | null | 29.9 | null |
1,454,086 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([N:9]2[C:16]3[C@@H:15]4[CH2:17][C@@H:14]4[CH2:13][C:12]=3[C:11]([C:18]([OH:20])=O)=[N:10]2)[CH:4]=1)#[N:2].[NH2:21][C@@H:22]([CH:25]([CH3:27])[CH3:26])[CH2:23][OH:24].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[OH:24][CH2:23][C@@H:22]([NH:21][C:18]([... | CC(C)[C@H](N)CO | N#Cc1ccnc(-n2nc(C(=O)O)c3c2[C@@H]2C[C@@H]2C3)c1 | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 23 | 0.5 | To a solution of (1aR,5aR)-2-(4-cyano-pyridin-2-yl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid (50 mg, 0.188 mmol), (S)-2-amino-3-methylbutan-1-ol (19.37 mg, 0.188 mmol), and triethylamine (0.052 mL, 0.376 mmol) in DMF (2 mL) was added HATU (71.4 mg, 0.188 mmol). The mixture was stirred ... | CC(C)[C@@H](CO)NC(=O)c1nn(-c2cc(C#N)ccn2)c2c1C[C@H]1C[C@@H]21 | null | 80.2 | null |
90,017 | ord_dataset-aeb5378e6e67443e8a4f5c7a5ec3de51 | null | 1981-01-01T00:12:00 | true | [NH2:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].[C:7]1(=[O:17])[O:12][C:10](=[O:11])[C:9]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:8]12>>[CH:15]1[CH:16]=[C:8]([C:7]([NH:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5])=[O:17])[C:9]([C:10]([OH:12])=[O:11])=[CH:13][CH:14]=1 | O=C1OC(=O)c2ccccc21 | NCCC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 3 | 25 grams (0.28 mole) of β-alanine and 41.6 grams (0.28 mole) of phthalic anhydride were heated at 150° C. while stirring for three hours and then cooled. On recrystallizing with ethyl acetate, N-phthalyl-β-alanine was obtained in 90% yield (55 grams). | O=C(O)CCNC(=O)c1ccccc1C(=O)O | null | 90 | null |
1,656,837 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[C:3]=1[C:4]#[N:5].[C:16]([N:24]=[C:25]=[O:26])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[C:4]([C:3]1[C:6]([O:10][CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:7][CH:8]=[CH:9][C:2]=1[NH:1][C:25]([NH:24][C:16](=[O:23]... | CC(C)(C)COc1cccc(N)c1C#N | O=C=NC(=O)c1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Prepared as in Example 146a from 2-amino-6-(neopentyloxy)-benzonitrile (Example 217b) and benzoyl isocyanate in 96% yield as a white solid. MS 352 (MH+). | CC(C)(C)COc1cccc(NC(=O)NC(=O)c2ccccc2)c1C#N | null | 96 | null |
1,249,365 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [C:1]([O:5][C:6](=[O:9])[CH2:7][NH2:8])([CH3:4])([CH3:3])[CH3:2].[CH:10]1([CH2:15][CH:16]=O)[CH2:14][CH2:13][CH2:12][CH2:11]1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:9])[CH2:7]/[N:8]=[CH:16]/[CH2:15][CH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1)([CH3:4])([CH3:3])[CH3:2] | CC(C)(C)OC(=O)CN | O=CCC1CCCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | null | In a manner similar to the method described in Example 1a, glycine tert-butyl ester (0.7 g, 5 mmol) was reacted with 2-cyclopentylacetaldehyde (Betapharma) (0.9 g, 8 mmol) in CH2Cl2 at room temperature for 20 h to give [2-cyclopentyl-eth-(E)-ylideneamino]-acetic acid tert-butyl ester as a colorless oil (1 g, 90%). | CC(C)(C)OC(=O)C/N=C/CC1CCCC1 | null | 88.8 | null |
1,648,577 | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | null | 2015-01-01T00:10:00 | true | [C:1]1([NH:7][C:8]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:16]1([CH2:22][CH2:23][CH:24]=O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[C:1]1([NH:7][C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH2:24][CH2:23][CH2:22][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11]... | O=CCCc1ccccc1 | O=C(Nc1ccccc1)N1CCNCC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared from piperazine-1-carboxylic acid phenylamide and 3-phenylpropionaldehyde. 1H NMR (400 MHz, CDCl3): 7.36-7.16 (m, 9H), 7.05-7.00 (m, 1H), 6.40 (br s, 1H), 3.52-3.47 (m, 4H), 2.65 (t, J=7.6 Hz, 2H), 2.47-2.38 (m, 4H), 2.39 (t, J=7.4 Hz, 2H), 1.88-1.79 (m, 2H). | O=C(Nc1ccccc1)N1CCN(CCCc2ccccc2)CC1 | null | null | null |
1,598,885 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [CH3:1][O:2][C:3]([N:5]1[C@@H:13]2[C@@H:8]([C@@:9]([OH:23])([C:14]#[C:15][C:16]3[CH:17]=[C:18]([CH3:22])[CH:19]=[CH:20][CH:21]=3)[CH2:10][CH2:11][CH2:12]2)[CH2:7][CH2:6]1)=[O:4].[CH3:24][NH:25][C:26](=[O:32])[CH2:27][CH2:28][C:29](O)=[O:30]>>[CH3:24][NH:25][C:26](=[O:32])[CH2:27][CH2:28][C:29]([O:23][C@@:9]1([C:14]#[C:... | COC(=O)N1CC[C@H]2[C@@H]1CCC[C@]2(O)C#Cc1cccc(C)c1 | CNC(=O)CCC(=O)O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Synthesis in analogy to the General Method 1 starting from (3aS,4R,7aS)-4-hydroxy-4-m-tolylethynyl-octahydro-indole-1-carboxylic acid methyl ester and N-methylsuccinamic acid to yield (3aR,4S,7aR)-methyl 4-(4-(methylamino)-4-oxobutanoyloxy)-4-(m-tolylethynyl)octahydro-1H-indole-1-carboxylate. MS [M+H]=427; RT=1.06 min;... | CNC(=O)CCC(=O)O[C@@]1(C#Cc2cccc(C)c2)CCC[C@@H]2[C@H]1CCN2C(=O)OC | null | null | null |
206,698 | ord_dataset-dd1de64954674e17b4b690cac09dc67b | null | 1990-01-01T00:04:00 | true | [C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:4])[CH2:2][CH3:3].CO[CH:13](OC)[N:14]([CH3:16])[CH3:15]>>[CH3:16][N:14]([CH3:15])[CH:13]=[C:2]([CH3:3])[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4] | CCC(=O)c1ccccc1 | COC(OC)N(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 57.0 g of propiophenone in 150 ml of N,N-dimethylformamide dimethyl acetal was stirred and heated at reflux for 24 hours. Then the solvent was removed in vacuo to give a yellow oil. The oil was subjected to Kugelrohr distillation to give 69.8 g of 3-dimethylamino-2-methylacrylophenone as a yellow oil, B.P.... | CC(=CN(C)C)C(=O)c1ccccc1 | null | null | null |
126,974 | ord_dataset-3e4cbfe3ea40460399482e6cf2f9c894 | null | 1985-01-01T00:02:00 | true | C[O:2][C:3](=[O:29])[C:4]([N+:26]([O-:28])=[O:27])([O:6][C:7]1[CH:12]=[C:11]([O:13][C:14]2[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][C:15]=2[Cl:25])[CH:10]=[CH:9][CH:8]=1)[CH3:5].[OH-].[Na+].O>C(#N)C>[Cl:20][C:19]1[CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=[C:15]([Cl:25])[C:14]=1[O:13]... | COC(=O)C(C)(Oc1cccc(Oc2c(Cl)cc(C(F)(F)F)cc2Cl)c1)[N+](=O)[O-] | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | O | null | null | null | null | null | null | null | null | null | null | null | 135 g (0.3 mol) of 5-(2,6-dichloro-4-trifluoromethylphenoxy)-2-nitro-α-phenoxy-propionic acid methyl ester and 30 ml of concentrated aqueous sodium hydroxide solution were stirred in 400 ml of acetonitrile and 150 ml of water at 20° C. for 24 hours. The solution was concentrated, the residue was taken up in 500 ml of w... | CC(Oc1cccc(Oc2c(Cl)cc(C(F)(F)F)cc2Cl)c1)(C(=O)O)[N+](=O)[O-] | null | 70.4 | null |
1,768,947 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [CH:1]1([C:4]2[N:8]3[CH2:9][CH2:10][CH2:11][C@@H:12]([C:13]4[N:17]5[CH:18]=[CH:19][N:20]=[C:21]([NH:22]CC6C=CC(OC)=CC=6OC)[C:16]5=[C:15]([C:34]5[CH:52]=[CH:51][C:37]([C:38]([NH:40][C:41]6[CH:46]=[C:45]([C:47]([F:50])([F:49])[F:48])[CH:44]=[CH:43][N:42]=6)=[O:39])=[CH:36][CH:35]=5)[N:14]=4)[C:7]3=[N:6][N:5]=2)[CH2:3][CH... | COc1ccc(CNc2nccn3c([C@@H]4CCCn5c(C6CC6)nnc54)nc(-c4ccc(C(=O)Nc5cc(C(F)(F)F)ccn5)cc4)c23)c(OC)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | A solution of (S)-4-(3-(3-cyclopropyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyridin-8-yl)-8-((2,4-dimethoxybenzyl)amino)imidazo[1,5-a]pyrazin-1-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide (30 mg, 0.04 mmol) in TFA (1.5 mL) was stirred at 110° C. for 2 hrs. The reaction mixture was purified by Pre-HPLC to give t... | Nc1nccn2c([C@@H]3CCCn4c(C5CC5)nnc43)nc(-c3ccc(C(=O)Nc4cc(C(F)(F)F)ccn4)cc3)c12 | null | null | null |
1,197,115 | ord_dataset-4e81c470cc3b429faf5e1caa50f70a98 | null | 2012-01-01T00:08:00 | true | C([O:5][C:6](=[O:19])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:18])[NH:16][CH3:17])=[CH:11][N:10]=1)(C)(C)C.[ClH:20]>O1CCOCC1>[ClH:20].[CH3:17][NH:16][C:15]([C:12]1[CH:13]=[CH:14][C:9]([CH2:8][CH2:7][C:6]([OH:19])=[O:5])=[N:10][CH:11]=1)=[O:18] | CNC(=O)c1ccc(CCC(=O)OC(C)(C)C)nc1 | null | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | null | null | null | null | null | null | null | null | null | null | null | 8 | tert-Butyl-3(5-methylcarbamoyl-pyridin-2-yl)propionate (0.29 g, 1.10 mmol) was dissolved in 10 mL of a 4 N hydrogen chloride solution in dioxane and stirred overnight. Evaporation of the solvent gave 0.27 mg of 3(5-methylcarbamoyl-pyridin-2-yl)propionic acid hydrochloride. LCMS 209 (M+1) | CNC(=O)c1ccc(CCC(=O)O)nc1 | null | null | null |
1,222,900 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:25][CH2:26][C:27]1[C:28]([F:44])=[C:29]([O:34][C:35]2[CH:36]=[C:37]([CH:40]=[C:41]([Cl:43])[CH:42]=2)[C:38]#[N:39])[C:30]([Cl:33])=[CH:31][CH:32]=1.CC(OC([N:52]1[C:60]2[C:55](=[CH:56][CH:57]=[C:58]([NH:61][S:62]([CH3:65])(=[O:64])=[O:63])[CH:59]=2)[CH:54]=[C:5... | CC(C)(C)OC(=O)n1c(C(=O)O)cc2ccc(NS(C)(=O)=O)cc21 | N#Cc1cc(Cl)cc(Oc2c(Cl)ccc(CN)c2F)c1 | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 25 | 8 | HATU (0.083 g, 0.218 mmol) was added to a solution of 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.045 g, 0.146 mmol), 1-{[(1,1-dimethylethyl)oxy]carbonyl}-6-[(methylsulfonyl)amino]-1H-indole-2-carboxylic acid (0.037 g, 0.146 mmol) and diisopropylethylamine (0.038 mL, 0.218 mmol) in DMF (1 m... | CS(=O)(=O)Nc1ccc2cc(C(=O)NCc3ccc(Cl)c(Oc4cc(Cl)cc(C#N)c4)c3F)[nH]c2c1 | null | 45 | null |
1,285,746 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([F:23])=[C:17]([N+:20]([O-])=O)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1)#[CH:2].O.O.Cl[Sn]Cl.C([O-])(O)=O.[Na+]>C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([F:23])=[C:17]([NH2:20])[CH:18]=3)[N:13]=[CH:12]... | C#Cc1cccc(Nc2ncnc3cc(F)c([N+](=O)[O-])cc23)c1 | null | null | Cl[Sn]Cl | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 25 | null | A mixture of N-(3-ethynylphenyl)-7-fluoro-6-nitroquinazolin-4-amine (310 mg, 1 mmol) and SnCl2.2H2O (171 mg, 4.5 mmol) in ethyl acetate (35 mL) was refluxed for 2 h. After cooled to room temperature, the mixture was treated with 5% aqueous NaHCO3 to adjust its pH to 9-10, and then subjected to extraction with EtOAc. Th... | C#Cc1cccc(Nc2ncnc3cc(F)c(N)cc23)c1 | null | 80.9 | null |
1,463,166 | ord_dataset-fd1fa959d6264608b0b7fcda16741bfd | null | 2014-01-01T00:08:00 | true | Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]3[N:14]=[C:15]([O:17][CH:18]4[CH:22]5[O:23][CH2:24][CH:25]([OH:26])[CH:21]5[O:20][CH2:19]4)[NH:16][C:11]3=[CH:10][C:9]=2[Cl:27])=[CH:4][CH:3]=1.[C:28]([CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)#[CH:29].C(=O)([O-])[O-].[Cs+].[Cs+]>[Cu]I>[Cl:27][C:9]1[CH:10]=[C:11]2[NH... | C#CC1CCNCC1 | OC1COC2C(Oc3nc4nc(-c5ccc(Br)cc5)c(Cl)cc4[nH]3)COC12 | null | [Cu]I | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 50 | 2 | 3R,3aR,6R,6aR)-6-((5-(4-bromophenyl)-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-ol (25 mg, 0.055 mmol), 4-ethynylpiperidine (10.5 mg, 0.072 mmol), copper (I) iodide (2.1 mg, 0.011 mmol), chloro(tri-tert-butyl)-2-[-(2′amino-1,1′-biphenyl)]palladium (II) (5.7 mg, 0.011 mmol, prepared by a proc... | O[C@@H]1CO[C@H]2[C@@H]1OC[C@H]2Oc1nc2nc(-c3ccc(C#CC4CCNCC4)cc3)c(Cl)cc2[nH]1 | null | null | null |
246,804 | ord_dataset-75ca79f43dad4cc8a934fe6487fa8eb1 | null | 1992-01-01T00:05:00 | true | Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])=[C:4]([NH:19][CH3:20])[N:3]=1.[NH3:21]>>[NH2:21][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])=[C:4]([NH:19][CH3:20])[N:3]=1 | N | CNc1nc(Cl)nc2c1ncn2Cc1ccccc1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In a manner analogous to that described in Example 2 it is also possible, by reacting 2-chloro-9-(2-fluorobenzyl)-6-(N-methylamino)-9H-purine (Example 6) with ammonia, to obtain the 2-amino-9-(2-fluorobenzyl)-6-(N-methylamino)-9H-purine, which has a melting range of from 207° to 208°. | CNc1nc(N)nc2c1ncn2Cc1ccccc1F | null | null | null |
1,680,041 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | [C:1]([O-:4])(=[O:3])[CH3:2].[NH4+].[CH3:6][C:7]#N>>[CH2:2]1[CH2:1][O:4][CH2:7][CH2:6]1.[O:3]1[CH2:7][CH2:6][CH2:2][CH2:1]1 | CC(=O)[O-] | CC#N | null | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 0.04 | Analytical HPLC/MS Analytical HPLC/MS was performed on a system consisting of a Waters Acquity UPLC, Waters Micromass LCT Premier XE mass spectrometer, Waters Acquity PDA. Column: Acquity UPLC HSS T3 1.8 μm; 2.1×50 mm; solventsystem: A=10 mM Ammonium acetate+0.1% HCOOH and B═CH3CN+0.1% HCOOH; flow rate=0.7 mL/min; meth... | C1CCOC1 | null | null | null |
1,269,220 | ord_dataset-d3580a12b15e46cc91aa73f4f1a4a8cc | null | 2013-01-01T00:03:00 | true | [N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[C:13]1[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C@H:20]2[CH2:25][CH2:24][C@H:23]([OH:26])[CH2:22][CH2:21]2)[N:14]=1)([O-])=O.CCO.[Cl-].[NH4+]>[Fe].O>[NH2:1][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[C:13]1[CH:18]=[CH:17][N:16]=[C:15]([NH... | O=[N+]([O-])c1cccc2c1ccn2-c1ccnc(N[C@H]2CC[C@H](O)CC2)n1 | null | null | [Fe] | [Cl-] | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | 80 | 24 | A mixture of trans-4-[4-(4-nitroindol-1-yl)-pyrimidin-2-ylamino]-cyclohexanol (2.44 g), EtOH (35 mL) and water (11 mL) was heated to 80° C. To the hot suspension was added ammonium chloride (1.46 g) followed by iron(0) (Fisher, 1.55 g) and the resulting mixture heated to 80° C. for 2 h, then to 50° C. for an additional... | Nc1cccc2c1ccn2-c1ccnc(N[C@H]2CC[C@H](O)CC2)n1 | null | null | null |
75,099 | ord_dataset-b9d8ddf9c2884d40859b6b5f24815a7d | null | 1980-01-01T00:12:00 | true | [CH3:1][C:2]([CH2:4][NH:5][C:6]1[C:11]([Cl:12])=[N:10][CH:9]=[CH:8][N:7]=1)=O>FC(F)(F)C(OC(=O)C(F)(F)F)=O>[Cl:12][C:11]1[C:6]2[N:7]([C:2]([CH3:1])=[CH:4][N:5]=2)[CH:8]=[CH:9][N:10]=1 | CC(=O)CNc1nccnc1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(OC(=O)C(F)(F)F)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | A 2.67 g (0.01 mol) sample of 3-chloro-2-(2-oxo-1-propanamino)pyrazine is dissolved in 10 ml of trifluoroacetic anhydride under nitrogen and after the exothermic reaction subsides, the mixture is concentrated under vacuum. The residue is partitioned between chloroform and aqueous sodium bicarbonate, and the chloroform ... | Cc1cnc2c(Cl)nccn12 | null | null | null |
11,751 | ord_dataset-7c810806c4564bada4a9550135bbb06f | null | 1976-01-01T00:08:00 | true | N1C=CC=CC=1.[C:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([CH:22]([OH:24])[CH3:23])[CH:16]([CH2:19][O:20][CH3:21])[CH2:17][OH:18])#[N:8]>[O-2].[O-2].[O-2].[Cr+6].ClCCl>[C:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH:15]([C:22]([CH3:23])=[O:24])[CH:16]([CH2:19][O:20][CH3:21])[CH:17]=[O:18])#[N:8] | COCC(CO)C(CCCCCCC#N)C(C)O | null | null | [Cr+6] | [O-2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 0.25 | To a mixture of 1.874 g. of pyridine (dried over barium oxide) and 60 ml. of dichloromethane (dried over calcium chloride) was added in one portion 1.237 g. of chromium trioxide (dried over phosphorus pentoxide). The mixture was stirred at room temperature for 15 mins. then 0.255 g. of 3-(6-cyanohexyl)-2-methoxymethyl-... | COCC(C=O)C(CCCCCCC#N)C(C)=O | null | 78 | null |
775,521 | ord_dataset-bf316bf78f4f45d4b275959c08104b7c | null | 2007-01-01T00:06:00 | true | C[O:2][C:3](=[O:28])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:22]=[C:21]([CH:23]=[CH2:24])[C:20]3[C:19](=[O:25])[CH2:18][CH2:17][C:16]([CH3:27])([CH3:26])[C:15]=3[CH:14]=2)=[CH:7][CH:6]=1.[OH-].[Li+]>CO.O1CCCC1>[CH3:26][C:16]1([CH3:27])[C:15]2[CH:14]=[C:13]([C:12]#[C:11][C:8]3[CH:7]=[CH:6][C:5]([CH2:4][C... | C=Cc1cc(C#Cc2ccc(CC(=O)OC)cc2)cc2c1C(=O)CCC2(C)C | null | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CO | null | null | null | null | null | null | null | null | null | 25 | 1.5 | A solution of [4-(8,8-dimethyl-5-oxo-4-vinyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl)-phenyl]-acetic acid methyl ester (Intermediate 70, 0.082 g, 0.22 mmol) in methanol (3 mL) and tetrahydrofuran (3 mL) was treated with a 2M solution of lithium hydroxide (1.5 mL, 3 mmol) and the resulting reaction mixture was stirred... | C=Cc1cc(C#Cc2ccc(CC(=O)O)cc2)cc2c1C(=O)CCC2(C)C | null | 82.4 | null |
1,719,142 | ord_dataset-3f2a531ffbae4b9eb1048afcd7953beb | null | 2016-01-01T00:04:00 | true | [Cl:1][C:2]1[N:3]=[C:4]2[NH:12][C@H:11]([C:13]([F:16])([F:15])[F:14])[CH2:10][CH2:9][N:5]2[C:6](=[O:8])[CH:7]=1.Br.Br[CH2:19][C:20]([C:22]1[CH:31]=[N:30][C:29]2[NH:28][CH2:27][CH2:26][O:25][C:24]=2[CH:23]=1)=[O:21]>>[Cl:1][C:2]1[N:3]=[C:4]2[N:12]([CH2:19][C:20]([C:22]3[CH:31]=[N:30][C:29]4[NH:28][CH2:27][CH2:26][O:25][... | O=c1cc(Cl)nc2n1CC[C@@H](C(F)(F)F)N2 | O=C(CBr)c1cnc2c(c1)OCCN2 | null | Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 200 mg (0.79 mmol) of (8S)-2-chloro-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one and 319.86 mg (0.95 mmol) of 2-bromo-1-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)ethanone hydrobromide were used in the reaction. After purification by chromatography on silica gel (eluent: 90/10 DCM/MeOH), 110 mg... | O=C(CN1c2nc(Cl)cc(=O)n2CC[C@H]1C(F)(F)F)c1cnc2c(c1)OCCN2 | null | null | null |
303,321 | ord_dataset-bfcf5a01f1a04ec585ba3f28cb93c8c9 | null | 1995-01-01T00:01:00 | true | [C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6][C:5](=[O:12])[O:4][C:2]2=[O:3].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH2:13]([C:1]12[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]1[NH:6][C:5](=[O:12])[O:4][C:2]2=[O:3])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1 | O=c1[nH]c2ccccc2c(=O)o1 | BrCc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following the procedure set forth in Step (2) of Preparation A, isatoic anhydride was reacted with benzyl bromide to give 1-benzyl-isatoic anhydride. | O=C1NC2C=CC=CC2(Cc2ccccc2)C(=O)O1 | null | null | null |
1,028,225 | ord_dataset-83acb82dc5ba4f7aba439b9875aaac43 | null | 2011-01-01T00:02:00 | true | [CH3:1][C:2]1([CH3:14])[O:6][C@H:5](/[CH:7]=[CH:8]/[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:4][O:3]1>[Pd].CO>[CH3:1][C:2]1([CH3:14])[O:6][C@H:5]([CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:4][O:3]1 | CCOC(=O)/C=C/[C@@H]1COC(C)(C)O1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | 8 | To a methanol (200 mL) solution of ethyl (2E)-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate (15.3 g, 76.7 mmol) was added 10% palladium on carbon (1.5 g). The reaction mixture was stirred under an atmosphere of hydrogen overnight. The catalyst was removed by filtration, and the solvent was removed in vacuo. Chromatog... | CCOC(=O)CC[C@@H]1COC(C)(C)O1 | null | null | null |
446,565 | ord_dataset-a4f0b79f6b9847168861270b79f84afa | null | 1999-01-01T00:11:00 | true | [F:1][C:2]([F:14])([F:13])[C:3]1[CH:12]=[CH:11][C:6](/[CH:7]=[CH:8]/[CH2:9][OH:10])=[CH:5][CH:4]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[F:1][C:2]([F:13])([F:14])[C:3]1[CH:12]=[CH:11][C:6](/[CH:7]=[CH:8]/[CH:9]=[O:10])=[CH:5][CH:4]=1 | OC/C=C/c1ccc(C(F)(F)F)cc1 | null | null | [Mn+4] | [O-2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | null | 0.25 | In 30 ml of methylene chloride were dissolved 2.15 g of trans-4-(trifluoromethyl)cinnamyl alcohol, and 14 g of active manganese dioxide were added to the solution at 0° C., followed by stirring of the resulting mixture for 15 minutes and then stirring at room temperature for 2 hours. The solid was removed by filtration... | O=C/C=C/c1ccc(C(F)(F)F)cc1 | null | 90 | null |
492,143 | ord_dataset-3f9174c7efcb4f31becbd3516cde9572 | null | 2001-01-01T00:02:00 | true | [CH:1]1([C:7]([CH:9]([OH:14])[CH2:10][CH2:11][CH:12]=[CH2:13])=[CH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CCCCCC.O=[Mn]=O>[CH:1]1([C:7]([C:9](=[O:14])[CH2:10][CH2:11][CH:12]=[CH2:13])=[CH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1 | C=CCCC(O)C(=C)C1CCCCC1 | null | null | O=[Mn]=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCCC | null | null | null | null | null | null | null | null | null | null | null | 96 | 2-Cyclohexyl-hepta-1,6-dien-3-ol (85 g, 0.44 mol) were oxidized with MnO2 (804 g, 9.2 mol) in 2 l of hexane at RT. After stirring for 96 hours, the reaction mixture was filtered over Celite and concentrated in vacuo yielding 71 g of a yellow oil. Distillation (0.04 Torr/70° C.) yielded 43.5 g (51%) of pure product. | C=CCCC(=O)C(=C)C1CCCCC1 | null | 83.9 | null |
168,252 | ord_dataset-01dbb772c5e249108f0b191ed17a2c0c | null | 1988-01-01T00:02:00 | true | [C:1]([NH2:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:11][C:12](=O)[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)(O)[O-].[Na+]>>[C:2]1([C:1]2[O:8][CH:11]=[C:12]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | NC(=O)c1ccccc1 | CCOC(=O)CC(=O)CCl | null | O=C([O-])O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 120 | null | A mixture of benzamide (60.0 g) and ethyl 4-chloroacetoacetate (49.4 g) was heated at 120° C. for 2 hours. After cooling, aqueous sodium bicarbonate solution was added thereto and the mixture was extracted with ethyl acetate. The extract was washed with water, dried (MgSO4) and concentrated. The residue was purified by... | CCOC(=O)Cc1coc(-c2ccccc2)n1 | null | 38 | null |
677,700 | ord_dataset-50cdc205280641d2a3e264f32908e3d0 | null | 2005-01-01T00:07:00 | true | [CH2:1]([O:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([CH:17]([NH:30][C:31]2[CH:38]=[CH:37][C:34]([C:35]#[N:36])=[CH:33][CH:32]=2)[CH2:18][N:19]2C(=O)C3C(=CC=CC=3)C2=O)=[C:11]([N+:39]([O-:41])=[O:40])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>C(O)C>[NH2:19][CH2:18][CH:17]([NH:30][C:31]1[CH:32]=[CH:33][C:... | COc1cc(C(CN2C(=O)c3ccccc3C2=O)Nc2ccc(C#N)cc2)c([N+](=O)[O-])cc1OCc1ccccc1 | null | null | NN | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | 60 | 48 | 4-[1-(4-Benzyloxy-5-methoxy-2-nitro-phenyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethylamino]-benzonitrile (2.7 g, 5 mmoles) was dissolved in ethanol (100 ml) and hydrazine hydrate (0.65 ml, 20 mmoles) added. The reaction was heated to 60° C. for 3 hours then at room temperature for 48 hours. The solids that precipit... | COc1cc(C(CN)Nc2ccc(C#N)cc2)c([N+](=O)[O-])cc1OCc1ccccc1 | null | 71.7 | null |
1,454,007 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | C([O:3][C:4]([C:6]1[C:7]2[CH2:8][C@H:9]3[CH2:22][C@H:10]3[C:11]=2[N:12]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[F:21])[N:13]=1)=O)C.[NH3:23]>>[F:21][C:15]1[CH:16]=[C:17]([F:20])[CH:18]=[CH:19][C:14]=1[N:12]1[C:11]2[C@@H:10]3[CH2:22][C@@H:9]3[CH2:8][C:7]=2[C:6]([C:4]([NH2:23])=[O:3])=[N:13]1 | N | CCOC(=O)c1nn(-c2ccc(F)cc2F)c2c1C[C@H]1C[C@@H]21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 100 | null | (1aR,5aR)-2-(2,4-Difluoro-phenyl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid ethyl ester (200 mg, 0.657 mmol) was partially dissolved in a 7 M methanolic solution of ammonia (2 mL, 14.00 mmol). The mixture was heated under microwave irradiation in a sealed, thick-walled glass tube for 1 ... | NC(=O)c1nn(-c2ccc(F)cc2F)c2c1C[C@H]1C[C@@H]21 | null | 67.5 | null |
954,687 | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | null | 2010-01-01T00:04:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](=[CH:11]/[C:12]2[NH:13][CH:14]=[CH:15][CH:16]=2)/[C:9]#[N:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:23][C:24]([CH3:28])=[CH:25][CH2:26]Br>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](=[CH:11]/[C:12]2[N:13]([CH2:26][CH:25]=[C:24]([CH3:28])[CH3:23])[CH:14]=[CH:15][CH:16]=2)... | CC(C)=CCBr | N#C/C(=C\c1ccc[nH]1)c1ccc(Cl)cc1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)=O | null | null | null | null | null | null | null | null | null | null | 25 | null | A solution of (Z)-2-(4-Chloro-phenyl)-3-(1H-pyrrol-2-yl)acrylonitrile being Compound 2 in Table 8 (200 mg, 0.875 mmol) in dry acetone (35 ml) was treated with K2CO3 (121 mg) followed by dimethylallyl bromide (111 μl, 0.962 mmol, 1.1 equivalents). The mixture was heated to a gentle reflux for 20 h. The reaction was cool... | CC(C)=CCn1cccc1/C=C(\C#N)c1ccc(Cl)cc1 | null | null | null |
1,018,717 | ord_dataset-f024e9664ab64906a71a2ff6004cb3d0 | null | 2010-01-01T00:12:00 | true | N#N.Br[C:4]1[C:12]2[O:11][C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1.[Li]CCCC.CON(C)[C:25]([C@@H:27]1[CH2:32][CH2:31][CH2:30][N:29]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:28]1)=[O:26]>C1COCC1>[C:13]([C:10]1[O:11][C:12]2[C:4]([C:25]([C@@H:27]3[CH2:32][CH2:31][CH2:3... | CC(C)(C)c1cc2cccc(Br)c2o1 | CON(C)C(=O)[C@@H]1CCCN(C(=O)OC(C)(C)C)C1 | null | N#N | [Li]CCCC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | -78 | 1 | Under protection of N2, a solution of 7-bromo-2-tert-butyl-benzofuran (0.5 g, 1.98 mmol) in anhydrous THF (5 mL) was cooled to −78° C. and 2.5 M n-BuLi solution in hexanes (0.87 mL, 2.18 mmol) was added dropwise slowly. The reaction mixture was stirred at −78° C. for 1 h and a solution of (R)-tert-butyl 3-(methoxy(meth... | CC(C)(C)OC(=O)N1CCC[C@@H](C(=O)c2cccc3cc(C(C)(C)C)oc23)C1 | null | 53.7 | null |
797,129 | ord_dataset-a2d74266062e4398bc26c4f876903ab8 | null | 2007-01-01T00:11:00 | true | C[O:2][C:3](=[O:36])[CH2:4][NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]([CH2:25][C:26]2[C:31]([CH3:32])=[CH:30][C:29]([CH3:33])=[CH:28][N:27]=2)[CH:15]2[C:24]3[N:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH2:18][CH2:17][CH2:16]2)=[C:9]([CH2:34][OH:35])[CH:8]=1.Cl>CCO.[OH-].[Na+]>[CH3:32][C:31]1[C:26]([CH2:25][N:14]... | COC(=O)CNCc1ccc(CN(Cc2ncc(C)cc2C)C2CCCc3cccnc32)c(CO)c1 | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 90 | 16 | (4-{[(3,5-Dimethyl-pyridin-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-3-hydroxymethyl-benzylamino)-acetic acid methyl ester (0.140 g, 0.29 mmol) was dissolved in a mixture of EtOH (3 mL) and 3M NaOH (7 mL). The colorless mixture was stirred at 90° C. for 16 hours to give an orange/brown solution. 3M ... | Cc1cnc(CN(Cc2ccc(CNCC(=O)O)cc2CO)C2CCCc3cccnc32)c(C)c1 | null | 77 | null |
126,868 | ord_dataset-3e4cbfe3ea40460399482e6cf2f9c894 | null | 1985-01-01T00:02:00 | true | [C:1]([NH:3][C:4]([NH:12][C:13]1[S:14][C:15]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:16]=2[N:17]=1)=[N:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)#[N:2]>O1CCCC1>[NH:2]=[C:1]1[N:17]2[C:13]([S:14][C:15]3[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:16]=32)=[N:12][C:4]([NH:5][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C... | COc1ccc2nc(NC(=Nc3ccccc3)NC#N)sc2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | null | 1 | Silica gel (chromatography grade) (20 g) was added to a solution of the product of step (c) (1.2 g) in tetrahydrofuran (50 ml) and the suspension stirred for 1 hour. The mixture was filtered, the filtrate evaporated to dryness and the residue triturated with methanol to yield a white solid. Recrystallisation of the sol... | COc1ccc2c(c1)sc1nc(Nc3ccccc3)nc(=N)n12 | null | 100 | null |
247,292 | ord_dataset-75ca79f43dad4cc8a934fe6487fa8eb1 | null | 1992-01-01T00:05:00 | true | [CH2:1]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[CH:12]([S:14]([F:17])(=[O:16])=[O:15])=[CH2:13].[ClH:18].CC(O)C>CN(C=O)C.CC(O)C>[ClH:18].[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([NH:9][CH:13]=[CH:12][S:14]([F:17])(=[O:16])=[O:15])=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4] | C=CS(=O)(=O)F | CCCCc1ccc(N)cc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CC(C)O | null | null | null | null | null | null | null | null | null | null | null | The reaction between 4-butylaniline (3.51 g, 23.5 mmol) and ethenesulfonyl fluoride (3.3 mL, 30 mmol) was carried out in DMF (75 mL) as described in Example 16. There was obtained a dark oily residue which was dissolved in a minimal amount of IPA and treated with 1.1 equivalents of HCl/IPA. The title compound (4.66 g, ... | CCCCc1ccc(NC=CS(=O)(=O)F)cc1 | null | 67 | null |
1,388,130 | ord_dataset-31641fb65b34430fa7435229b949b604 | null | 2014-01-01T00:01:00 | true | Cl[C:2]1[C:11]2[C:6](=[C:7]([Cl:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]([F:22])([F:21])[C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][N:15]=2)[N:3]=1.[NH2:23][C:24]1[CH:28]=[C:27]([CH3:29])[N:26](C(OC(C)(C)C)=O)[N:25]=1.CC(O)=O>CC(N(C)C)=O>[Cl:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[C:4]([C:13]([F:22])([... | Fc1ccc(C(F)(F)c2nc(Cl)c3cccc(Cl)c3n2)nc1 | Cc1cc(N)nn1C(=O)OC(C)(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | CC(=O)N(C)C | null | null | null | null | null | null | null | null | null | 100 | null | To 4,8-dichloro-2-(difluoro(5-fluoropyridin-2-yl)methyl)quinazoline (263 mg, 0.77 mmol) in DMA (2.0 mL) were added tert-butyl 3-amino-5-methyl-1H-pyrazole-1-carboxylate (300 mg, 1.53 mmol) and HOAc (0.102 mL), and the mixture was heated at 100° C. for 5 h. The mixture was allowed to cool to rt and was purified by prepa... | Cc1cc(Nc2nc(C(F)(F)c3ccc(F)cn3)nc3c(Cl)cccc23)n[nH]1 | null | 16.4 | null |
1,298,997 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | C([O:3][C:4](=O)[CH2:5][NH:6][C:7]1[C:12]([C:13]#[N:14])=[CH:11][CH:10]=[CH:9][N:8]=1)C.C[O-].[Na+]>[Ni].CO>[NH:6]1[C:7]2[N:8]=[CH:9][CH:10]=[CH:11][C:12]=2[CH2:13][NH:14][C:4](=[O:3])[CH2:5]1 | CCOC(=O)CNc1ncccc1C#N | null | null | [Ni] | C[O-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | 25 | 48 | Raney nickel (3 g) was added to anhydrous methanol (50 mL) under argon and washed with anhydrous methanol (4×50 mL) (3-Cyanopyridin-2-ylamino)-acetic acid ethyl ester (3.35 g, 16.3 mmol) was dissolved in methanol (50 mL) and added to the Raney nickel slurry. The reaction vessel was purged with argon for 10 min. Sodium ... | O=C1CNc2ncccc2CN1 | null | 32 | null |
1,294,815 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | [CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][C:12]([Br:17])=[CH:11][CH:10]=2)=[O:5])[CH3:2].Cl.[CH3:19][O:20][C@@H:21]([CH3:24])[CH2:22][NH2:23].C(N(C(C)C)CC)(C)C>C(O)C>[Br:17][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[C:15]2[NH:23][CH2:22... | CCOC(=O)c1cnc2ccc(Br)cc2c1Cl | CO[C@@H](C)CN | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(C(C)C)C(C)C | CCO | null | null | null | null | null | null | null | null | null | null | 16 | Suspend ethyl-6-bromo-4-chloro-quinoline-3-carboxylate (389 g, 1.24 mol) and (2S)-2-methoxypropan-1-amine, hydrochloride (171 g, 1.36 mol, 1.1 eq.) in ethanol (5.84 L). Add diisopropylethylamine (474 mL) and heat the mixture at 50° C. overnight. After 16 hours, cool the reaction to room temperature and concentrate in v... | CCOC(=O)c1cnc2ccc(Br)cc2c1NC[C@H](C)OC | null | null | null |
697,306 | ord_dataset-4e9c2fa02a7544fd839206719263345f | null | 2006-01-01T00:02:00 | true | Cl[CH2:2][CH2:3][CH2:4][CH:5]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[N:6]1[S:17]([C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)(=[O:19])=[O:18].[NH:27]1[CH:31]=[N:30][N:29]=[N:28]1>>[F:16][C:13]1[CH:14]=[CH:15][C:10]([CH:7]2[N:6]([S:17]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26... | Cc1ccc(S(=O)(=O)N2C(CCCCl)CCC2c2ccc(F)cc2)cc1 | c1nnn[nH]1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound, colorless oil, MS: m/e=430.5 (M+H+), was prepared in accordance with the general method of example 82b from (2RS,5RS)-2-(3-chloro-propyl)-5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidine and 1H-tetrazole. | Cc1ccc(S(=O)(=O)N2C(CCCn3ncnn3)CCC2c2ccc(F)cc2)cc1 | null | null | null |
655,161 | ord_dataset-fe016e2f90e741a590ad77fd5933161f | null | 2004-01-01T00:11:00 | true | C[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([N:11]([S:13]([C:16]2[CH:21]=[CH:20][C:19](F)=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH3:12])[C:3]=1[CH3:23].[OH:24][CH2:25][CH2:26][CH2:27][CH2:28][NH:29][C:30]([C:32]1[CH:40]=[CH:39][C:35]2[O:36][CH2:37][O:38][C:34]=2[CH:33]=1)=[O:31]>>[O:36]1[C:35]2[CH:39]=[CH:40][C:... | Cc1ccc(C(=O)O)c(N(C)S(=O)(=O)c2ccc(F)cc2)c1C | O=C(NCCCCO)c1ccc2c(c1)OCO2 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The product of Example 2 (0.30 g, 0.92 mmol) was coupled to N-(4hydroxybutyl)-1,3-benzodioxole-5-carboxamide, prepared according to Example 21, (0.23 g, 0.96 mmol) using the procedure of Example 3 to provide 0.30 g (60% yield) of yellow solid. MP 110° C.; 1H NMR (DMSO-d6): δ 1.66-1.80 (m,CH2, CH2)1.89 (s, CH3), 3.1 (s,... | Cc1cccc(C(=O)O)c1N(C)S(=O)(=O)c1ccc(OCCCCNC(=O)c2ccc3c(c2)OCO3)cc1 | null | 60 | null |
109,926 | ord_dataset-406d20cb3f314e2c967b14f55925f895 | null | 1983-01-01T00:10:00 | true | [OH-].[Na+].[Br:3][C:4]([Br:16])=[CH:5][CH2:6][CH:7]([CH:13]([CH3:15])[CH3:14])[C:8]([O:10]CC)=[O:9]>O.C(O)C>[Br:3][C:4]([Br:16])=[CH:5][CH2:6][CH:7]([CH:13]([CH3:14])[CH3:15])[C:8]([OH:10])=[O:9] | CCOC(=O)C(CC=C(Br)Br)C(C)C | null | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | 25 | 8 | In a mixture of 7 g of water and 20 g of ethanol were dissolved 1.1 g of sodium hydroxide and 4.6 of the ethyl α-(3.3-dibromoallyl)isovalerate obtained above were added to the above solution. The mixture was stirred at room temperature overnight and, then, refluxed for 3 hours. The reaction mixture was then distilled t... | CC(C)C(CC=C(Br)Br)C(=O)O | null | 88 | null |
494,968 | ord_dataset-9df8b3ec9c8742b3802e0efaac6f6ef3 | null | 2001-01-01T00:03:00 | true | COC([NH:5][C@H:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH:15][C:16]([C:18]3[C:19]([C:25]4[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=4)=[C:20]([CH3:24])[CH:21]=[CH:22][CH:23]=3)=[O:17])[CH:12]=2)[CH2:7]1)=O.I[Si](C)(C)C.CO>C(#N)C>[NH2:5][C@H:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N... | COC(=O)N[C@@H]1Cc2ccc(NC(=O)c3cccc(C)c3-c3ccc(C(F)(F)F)cc3)cc2C1 | null | null | C[Si](C)(C)I | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | CO | null | null | null | null | null | null | null | null | null | 0 | 8 | (R)-6-methyl-4′-trifluoromethylbiphenyl-2-carboxylic acid (2-methoxycarbonylaminoindan-5-yl)-amide (6.5 g, 13.9 mmol) is dissolved in acetonitrile (325 mL) and cooled to 0° C. under nitrogen. Iodotrimethylsilane (11.1 g, 55.6 mmol) is added dropwise, the mixture is allowed to warm to room temperature and is stirred ove... | Cc1cccc(C(=O)Nc2ccc3c(c2)C[C@H](N)C3)c1-c1ccc(C(F)(F)F)cc1 | null | null | null |
1,228,237 | ord_dataset-cde802cdb7434a5f82a22981ccaefc4e | null | 2012-01-01T00:11:00 | true | [CH3:1][CH2:2][CH2:3]Br.[Br:5][C:6]1[CH:7]=[CH:8][C:9]([F:14])=[C:10]([CH:13]=1)[CH:11]=[O:12]>C(OCC)C.II>[Br:5][C:6]1[CH:7]=[CH:8][C:9]([F:14])=[C:10]([CH:11]([OH:12])[CH2:1][CH2:2][CH3:3])[CH:13]=1 | CCCBr | O=Cc1cc(Br)ccc1F | null | II | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOCC | null | null | null | null | null | null | null | null | null | null | 25 | 0.17 | To a suspension of Mg (0.236 g, 9.83 mmol) in diethyl ether (10 mL), I2 (1 spatula) was added n-propyl bromide (0.72 g, 0.53 mL, 5.9 mmol) at room temperature. When iodine color disappeared, the remaining n-propyl bromide in ether was added to the reaction mixture and stirred at room temperature for 10 minutes. To this... | CCCC(O)c1cc(Br)ccc1F | null | 93.8 | null |
1,644,595 | ord_dataset-bcc0b01d4f58457a8733b10a099f43ba | null | 2015-01-01T00:10:00 | true | [CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]2[C:17]([F:20])([F:19])[F:18])=[C:6]([N+:21]([O-])=O)[CH:5]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]2[C:17]([F:20])([F:18])[F:19])=[C:6]([NH... | COC(=O)c1ccc(NC2CCCCC2C(F)(F)F)c([N+](=O)[O-])c1 | null | null | [Pd] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | null | null | null | null | null | null | null | null | null | null | null | 16 | 1.63 g 3-Nitro-4-(2-trifluoromethyl-cyclohexylamino)-benzoic acid methyl ester were dissolved in 25 ml methanol, 0.03 g of palladium on carbon (10%) were added and the mixture was hydrogenated at 5 bar for 16 h. The catalyst was removed by filtration over celite, the filtrate was concentrated to obtain 1.44 g (97%) of ... | COC(=O)c1ccc(NC2CCCCC2C(F)(F)F)c(N)c1 | null | 96.7 | null |
913,490 | ord_dataset-c663259b80f947e2a8923796fb0e9a6b | null | 2009-01-01T00:10:00 | true | C(N(CC)CC)C.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[C:29]([NH:36][CH2:37][C:38]([OH:40])=O)([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30].[CH:41]1[C:49]2[C:48]3[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][C:47]=3[O:46][C:45]=2[CH:44]=[CH:43][C:42]=1[NH2:55]>>[O:40]=[C:38]([NH:55][C:42]1[CH:43]=[CH:44][C:45]2[O:46][C:47]3[CH... | CC(C)(C)OC(=O)NCC(=O)O | Nc1ccc2oc3c(c2c1)CCCCC3 | null | CCN=C=NCCCN(C)C | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | null | Following the procedure of Example 30, triethylamine (0.43 mL, 3.1 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (0.31 g, 1.6 mmol), N-hydroxybenzotriazole (0.22 g, 1.6 mmol), N-Boc-glycine (0.24 g, 1.4 mmol), and 7,8,9,10-tetrahydro-6H-benzo[b]-cyclohepta[d]furan-2-ylamine (0.25 g, 1.2 mmol) provided tert-butyl... | CC(C)(C)OC(=O)NCC(=O)Nc1ccc2oc3c(c2c1)CCCCC3 | null | 46.5 | null |
336,269 | ord_dataset-65c44df6676d4ce3a1874db5d7958ca9 | null | 1996-01-01T00:08:00 | true | [F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([S:13]([NH:16][C:17]2[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][C:18]=2[O:19][C:20]2[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=2[C:22](O)=[O:23])(=[O:15])=[O:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.B>O1CCCC1>[F:37][C:2]([F:1])([F:38])[C:3]1[CH:4]=[C:... | O=C(O)c1ccccc1Oc1ccc(C(F)(F)F)cc1NS(=O)(=O)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 | null | null | B | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | null | 2-[2-[3,5-Bis(trifluoromethyl)phenylsulfonamido]-4-trifluoromethylphenoxy]benzoic acid (0.1 g, 0.17 mmol) was dissolved in tetrahydrofuran (5 mL) and stirred under argon at room temperature. A 1M solution of borane (0.5 mL, 0.5 mmol) was added and the mixture was stirred for 16 h. Evaporation of the solvent followed by... | O=S(=O)(Nc1cc(C(F)(F)F)ccc1Oc1ccccc1CO)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 | null | null | null |
675,970 | ord_dataset-632f0d9054ce41aba87d4970966c34a6 | null | 2005-01-01T00:06:00 | true | OO.[F:3][C:4]([F:9])([F:8])[C:5]([O-:7])=[O:6].[K+].[F:11][C:12]([F:23])([F:22])[C:13]([O:15]C(=O)C(F)(F)F)=[O:14]>FC(F)(F)C(O)=O>[F:3][C:4]([F:9])([F:8])[C:5]([O:7][O:15][C:13](=[O:14])[C:12]([F:23])([F:22])[F:11])=[O:6] | O=C([O-])C(F)(F)F | O=C(OC(=O)C(F)(F)F)C(F)(F)F | null | OO | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | A solution of bis(trifluoroacetyl) peroxide in trifluoroacetic acid was prepared by addition of H2O2 (95%, 1.61 g, 45.0 mmol H2O2) dropwise into a well-stirred solution of potassium trifluoroacetate (6.8 mg, 0.045 mmol) in freshly distilled bis(trifluoroacetic) anhydride (21 g, 100 mmol) at 0° C. A 31% (mol) solution o... | O=C(OOC(=O)C(F)(F)F)C(F)(F)F | null | null | null |
1,236,894 | ord_dataset-e96f5a2842f14e5380461c234100f05a | null | 2012-01-01T00:12:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9]O.CC(C)(O)[C:13]#[N:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC=CC=1.CCCCCC>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:13]#[N:14] | OCCc1ccccc1Br | CC(C)(O)C#N | null | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCCCCC | c1ccccc1 | null | null | null | null | null | null | null | null | null | 25 | 12 | To a solution of commercially available 2-(2-bromophenyl)ethanol (1 eq.) in Benzene (0.064M) at room temperature was added acetone cyanohydrin (1.5 eq), 1-1′(Azodicarbonyl)dipiperidine (1.5 eq) then dropwise over 5 min triphenyl phosphine (1.5 eq). The mixture was stirred at room temperature for 12 h, diluted with hexa... | N#CCCc1ccccc1Br | null | null | null |
1,247,145 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [CH2:1]([C:5]1[C:9]([C:10]([F:13])([F:12])[F:11])=[C:8]([C:14]([OH:16])=O)[O:7][N:6]=1)[CH:2]([CH3:4])[CH3:3].N1C=CC=CC=1.[F:23]C1N=C(F)N=C(F)N=1>ClCCl>[CH2:1]([C:5]1[C:9]([C:10]([F:13])([F:12])[F:11])=[C:8]([C:14]([F:23])=[O:16])[O:7][N:6]=1)[CH:2]([CH3:4])[CH3:3] | Fc1nc(F)nc(F)n1 | CC(C)Cc1noc(C(=O)O)c1C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 8 | To a mixture of 3-isobutyl-4-(trifluoromethyl)isoxazole-5-carboxylic acid (0.200 g, 0.843 mmol) and pyridine (0.082 mL, 1.01 mmol) in dichloromethane (8 mL) at room temperature was added 2,4,6-trifluoro-1,3,5-triazine (cyanuric fluoride) (0.085 mL, 1.01 mmol). The reaction mixture was stirred at room temperature overni... | CC(C)Cc1noc(C(=O)F)c1C(F)(F)F | null | 64.5 | null |
212,594 | ord_dataset-e6e5ffd5405c481d8061087049155f9f | null | 1990-01-01T00:07:00 | true | [N:1]1([CH2:6][C:7]2[CH:8]=[CH:9][C:10]3[N:14]=[N:13][N:12]([O:15][CH2:16][CH2:17][CH2:18][C:19]([O:21]CC)=[O:20])[C:11]=3[CH:24]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[OH-].[Na+].Cl>C(O)C>[N:1]1([CH2:6][C:7]2[CH:8]=[CH:9][C:10]3[N:14]=[N:13][N:12]([O:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[C:11]=3[CH:24]=2)[CH:5]=[C... | CCOC(=O)CCCOn1nnc2ccc(Cn3ccnc3)cc21 | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | null | null | null | null | null | null | null | null | null | null | 25 | 1.5 | A mixture of 3.2 parts of ethyl 4-[[6-(1H-imidazol-1-ylmethyl)-1H-benzotriazol-1-yl]oxy]butanoate, 25 parts of a sodium hydroxide solution 1N and 20 parts of ethanol was stirred for 1.5 hours at room temperature. 25 Parts of hydrochloric acid solution 1N were added and the whole was concentrated to a volume of about 20... | O=C(O)CCCOn1nnc2ccc(Cn3ccnc3)cc21 | null | 71 | null |
1,682,607 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | C(N(C(C)C)CC)(C)C.[NH2:10][C@H:11]([C:27]([O:29][CH3:30])=[O:28])[CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].[NH:31]([C:48]([O:50][CH2:51][CH:52]1[C:64]2[C:59](=[CH:60][CH:61]=[CH:62][CH:63]=2)[C:58]2[C:53]1=[CH:54][CH:55]=[CH:56][CH:57]=2)=[O:49])[... | COC(=O)[C@@H](N)CCCCNC(=O)OCc1ccccc1 | CC(C)(C)Oc1ccc(C[C@H](NC(=O)OCC2c3ccccc3-c3ccccc32)C(=O)O)cc1 | null | CCN=C=NCCCN(C)C | Cl | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | 8 | To a solution of diisopropylethyl amine (1.19 mL, 3.43 mmol) in DCM (50 mL), was added Lys(Z)OMe (1.13 g, 3.43 mmol). To this solution was added FmocTyr(tBu)OH (1.50 g, 3.26 mmol), then HOBt (0.463 g, 3.43 mmol), and finally EDC.HCl (0.6571 g, 3.43 mmol). This solution was allowed to stir for 8 h at which time the orga... | COC(=O)[C@H](CCCCNC(=O)OCc1ccccc1)NC(=O)[C@H](Cc1ccc(OC(C)(C)C)cc1)NC(=O)OCC1c2ccccc2-c2ccccc21 | null | 97.5 | null |
380,165 | ord_dataset-993feac5ecf54388aa6326a220e46db3 | null | 1997-01-01T00:10:00 | true | [C:1]([NH:18][C@H:19]([C:23]([OH:25])=O)[CH:20]([CH3:22])[CH3:21])([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:51][C:52]1[S:56][C:55](=[S:57])[NH:54][N:53]=1>>[CH:7]1[C:6]2[CH:5]([CH2:4][O:3][C:1]([NH... | Nc1n[nH]c(=S)s1 | CC(C)[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O | null | C(=NC1CCCCC1)=NC1CCCCC1 | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Fmoc-Valine (0.68 grams), 1-hydroxybenzotriazole (0.36 grams), dicyclohexylcarbodiimide (0.42 grams) and 5-amino-1,3,4-thiadiazole-2-thione (0.4 grams) were reacted according to the procedures described in Example 1. The resulting product was recrystallized from ethanol-pentane. M.P. 141°-144° C. NMR spectrum (d6 -DMSO... | CC(C)[C@H](NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)Nc1n[nH]c(=S)s1 | null | null | null |
1,428,063 | ord_dataset-5e6956e6e8c24a168866a253f4a66c6c | null | 2014-01-01T00:05:00 | true | Cl.Cl.Cl.[O:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C@H:21]4[CH2:26][CH2:25][C@H:24]([NH2:27])[CH2:23][CH2:22]4)[CH2:15][CH2:14]3)[C:7]=2[O:6][CH2:5]1.[C:28](O)(=[O:31])[CH2:29][CH3:30]>>[O:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][... | CCC(=O)O | N[C@H]1CC[C@H](CCN2CCN(c3cccc4c3OCO4)CC2)CC1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound, white solid (10 mg, 48%), MS (ISP) m/z=388.3 [(M+H)+], was prepared in accordance with the general method of example 1 from Trans-4-[2-(4-Benzo[1,3]dioxol-4-yl-piperazin-1-yl)-ethyl]-cyclohexylamine hydrochloride (Intermediate A) (20 mg, 0.0543 mmol) and propionic acid. | CCC(=O)N[C@H]1CC[C@H](CCN2CCN(c3cccc4c3OCO4)CC2)CC1 | null | null | null |
515,176 | ord_dataset-41760195182e4bb4bc779bd722456071 | null | 2001-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=O)=[CH:5]2.Cl.[CH3:15][O:16][C:17](=[O:21])[CH:18]([CH3:20])[NH2:19]>>[CH3:15][O:16][C:17](=[O:21])[CH:18]([NH:19][C:11]([C:6]1[NH:7][C:8]2[C:4]([CH:5]=1)=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)=[O:13])[CH3:20] | O=C(O)c1cc2cc(Cl)ccc2[nH]1 | COC(=O)C(C)N | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | From 5chloro-1H-indole-2-carboxylic acid and DL-alanine methyl ester hydrochloride. | COC(=O)C(C)NC(=O)c1cc2cc(Cl)ccc2[nH]1 | null | null | null |
1,079,486 | ord_dataset-afd812677c134591a99f46ce28de2524 | null | 2011-01-01T00:08:00 | true | C(Cl)(=O)C(Cl)=O.[C:7]([C:11]1[CH:47]=[CH:46][C:14]([CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2/[CH:23]=[CH:24]/[CH:25]([CH2:37][C:38]2[CH:43]=[CH:42][C:41]([C:44]#[N:45])=[CH:40][CH:39]=2)[CH2:26][CH2:27][C:28]2[CH:36]=[CH:35][C:31]([C:32](O)=[O:33])=[CH:30][CH:29]=2)=[CH:13][CH:12]=1)([CH3:10])([CH3:9... | CC(C)(C)c1ccc(COc2ccccc2/C=C/C(CCc2ccc(C(=O)O)cc2)Cc2ccc(C#N)cc2)cc1 | NNC(N)=S | null | O=C(Cl)C(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 0.5 | 5.9 mg (0.05 mmol) of oxalyl chloride are slowly added dropwise to a solution of 12.7 mg (0.02 mmol) of 4-[(4E)-5-{2-[(4-tert-butylbenzyl)oxy]phenyl}-3-(4-cyanobenzyl)pent-4-en-1-yl]-benzoic acid from Example 100A in 0.2 ml of dry THF with 1 drop of DMF while cooling in ice. The reaction mixture is stirred at RT for 30... | CC(C)(C)c1ccc(COc2ccccc2/C=C/C(CCc2ccc(C(=O)NNC(N)=S)cc2)Cc2ccc(C#N)cc2)cc1 | null | null | null |
288,585 | ord_dataset-96711be098434bc9ab567cb77fa3362b | null | 1994-01-01T00:04:00 | true | [C:1]([C:3]1([CH2:18][CH2:19]Br)[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]1=2)#[N:2].[CH3:21][NH:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([C:3]1([CH2:18][CH2:19][N:22]([CH2:23][CH2:24][C:25]2[C... | N#CC1(CCBr)c2ccccc2CCc2ccccc21 | CNCCc1ccc(F)cc1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC#N | null | null | null | null | null | null | null | null | null | null | null | null | A mixture containing 1-[(5-cyano-10,11-dihydrodibenzo[a,d]cyclohepten-5-yl]-2-bromoethane (3.26 g -- see Preparation 26), N-methyl-4-fluorophenethylamine (1.53 g -- see C.A. 80:P120985y), anhydrous potassium carbonate (2.76 g) and acetonitrile (50 ml) was heated under reflux for 24 hours then concentrated in vacuo. Wat... | CN(CCc1ccc(F)cc1)CCC1(C#N)c2ccccc2CCc2ccccc21 | null | null | null |
6,849 | ord_dataset-653be8036d754ce7b8a1c4cd419eaf55 | null | 1976-01-01T00:05:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([I:19])[CH:17]=[CH:18][C:13]=2[N:12]([CH3:20])[C:11](=[O:21])[CH2:10][N:9]=1.C(O[CH:25](OCC)[N:26]([CH3:28])[CH3:27])C>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([I:19])[CH:17]=[CH:18][C:13]=2[N:12]([CH3:20])[C:11](=... | CN1C(=O)CN=C(c2ccccc2Cl)c2cc(I)ccc21 | CCOC(OCC)N(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 130 | null | A mixture consisting of 8 gm of 5-(2'-chloro-phenyl)-1,3-dihydro-7-iodo-1-methyl-2H-1,4-benzodiazepin-2-one and 16 ml of N,N-dimethyl-formamide-diethylacetal was heated for 90 minutes at 130°C. Thereafter, the reaction mixture was allowed to cool, and the crystalline substance which separated out was collected by vacuu... | CN(C)C=C1N=C(c2ccccc2Cl)c2cc(I)ccc2N(C)C1=O | null | null | null |
1,102,186 | ord_dataset-af85e6f81c2d49f08086afd6d9e6959c | null | 2011-01-01T00:10:00 | true | [NH2:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH:12]=[C:13]([NH:15][C:16]([CH:18]3[CH2:20][CH2:19]3)=[O:17])[N:14]=2)[N:11]=1.[C:24]([C:26]1([C:29]2[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=2)[C:32](O)=[O:33])[CH2:28][CH2:27]1)#[N:25].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O... | Nc1cccc(Oc2ccc3nc(NC(=O)C4CC4)cn3n2)c1 | N#CC1(c2cccc(C(=O)O)c2)CC1 | null | CCN=C=NCCCN(C)C | Cl | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | Using N-[6-(3-aminophenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (170 mg, 0.55 mmol), 3-(1-cyanocyclopropyl)benzoic acid (100 mg, 0.55 mmol), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (110 mg, 0.55 mmol), 1-hydroxybenzotriazole (74 mg, 0.55 mmol) and N,N-dimethylformamide (10 mL) as ... | N#CC1(c2cccc(C(=O)Nc3cccc(Oc4ccc5nc(NC(=O)C6CC6)cn5n4)c3)c2)CC1 | null | 46.4 | null |
1,618,916 | ord_dataset-35c51552812941cda45194a013d34bb9 | null | 2015-01-01T00:08:00 | true | [Si:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[F:20][C:21]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:22]=1[C:23]([NH:25][NH2:26])=[O:24].C(O)(=O)C>CCO>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][C:12](=[N:26][NH:25][C:23](=[O:24])[C:22... | CC(C)(C)[Si](C)(C)OCCCC(=O)c1ccccc1 | NNC(=O)c1cc(F)ccc1F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | CCO | null | null | null | null | null | null | null | null | null | 90 | 5 | To a solution of 4-(tert-butyldimethylsilanyloxy)-1-phenylbutan-1-one (420 mg, 1.5 mmol) in EtOH (4 mL) was added 2,5-difluorobenzoic acid hydrazide (260 mg, 1.5 mmol) and acetic acid (0.07 mL, 1.2 mmol). After stirring the reaction mixture at 90° C. for 5 hours, more acetic acid (0.1 mL) was added. The mixture was sti... | CC(C)(C)[Si](C)(C)OCCCC(=NNC(=O)c1cc(F)ccc1F)c1ccccc1 | null | null | null |
858,589 | ord_dataset-93908aaae836460ebd48d733eccad483 | null | 2009-01-01T00:01:00 | true | C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:15]=[C:16]([CH:45]=[CH:46][CH:47]=2)[NH:17][C:18](=[O:44])[CH2:19][CH2:20][CH2:21][NH:22][C:23]([N:25]2[CH:30]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)[C:29]([C:38]([O:40][CH3:41])=[O:39])=[C:28]([CH3:42])[NH:27][C:26]2=[O:43])=[O:24])[CH2:10][CH2:9]1)=O)(C)(C... | COC(=O)C1=C(C)NC(=O)N(C(=O)NCCCC(=O)Nc2cccc(C3CCN(C(=O)OC(C)(C)C)CC3)c2)C1c1ccc(F)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | 25 | 0.17 | Into a solution of methyl 3-{[(4-{3-[1-(tert-butoxycarbonyl)-4-piperidinyl]anilino}-4-oxobutyl)amino]carbonyl}-4-(4-fluorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate (40.9 mg, 0.0628 mmol) in dichloromethane (2.00 mL) at 0° C. was slowly added trifluoroacetic acid (71.6 mg, 0.628 mmol). The reacti... | COC(=O)C1=C(C)NC(=O)N(C(=O)NCCCC(=O)Nc2cccc(C3CCNCC3)c2)C1c1ccc(F)cc1 | null | 99.9 | null |
1,020,881 | ord_dataset-136cfada6ce247b4919085a57363459e | null | 2011-01-01T00:01:00 | true | COC1C=C(OC)C=CC=1C[NH:6][C:7]1[CH:16]=[N:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH3:17])[CH:13]=2)[N:8]=1.[C:24]([OH:30])([C:26]([F:29])([F:28])[F:27])=[O:25]>C(Cl)Cl>[F:27][C:26]([F:29])([F:28])[C:24]([OH:30])=[O:25].[CH3:17][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH2:6])[CH:16]=[N:15]2 | COc1ccc(CNc2cnc3cc(C)ccc3n2)c(OC)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | O=C(O)C(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | N-(2,4-Dimethoxybenzyl)-6-methylquinoxalin-2-amine (0.84 g, 2.72 mmol) was stirred in TFA (10 mL, 130 mmol)/CH2Cl2 (10 mL) at room temperature for 30 min. Solvents were removed on the rotary evaporator. Saturated aqueous Na2CO3 (200 mL) was added to the red residue, which then precipitated a tan solid. The mixture was ... | Cc1ccc2nc(N)cnc2c1 | null | 86.1 | null |
164,321 | ord_dataset-1385ebf1988241e49636101695ad79e4 | null | 1987-01-01T00:10:00 | true | [NH2:1][CH2:2][C:3]([OH:5])=[O:4].[Cl:6][C:7]1[C:17]([Cl:18])=[C:16]([C:19](=[O:24])[C:20](=[CH2:23])[CH2:21][CH3:22])[CH:15]=[CH:14][C:8]=1[O:9][CH2:10][C:11](Cl)=[O:12]>O1CCCC1>[Cl:6][C:7]1[C:17]([Cl:18])=[C:16]([C:19](=[O:24])[C:20](=[CH2:23])[CH2:21][CH3:22])[CH:15]=[CH:14][C:8]=1[O:9][CH2:10][C:11]([NH:1][CH2:2][C... | NCC(=O)O | C=C(CC)C(=O)c1ccc(OCC(=O)Cl)c(Cl)c1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 25 | 2.25 | To a stirring suspension of finely ground glycine (6.01 g, 0.08 mole) in tetrahydrofuran (50 ml) was added, dropwise, the solution of [2,3-dichloro-4-(2-methylenebutyryl)phenoxy]acetyl chloride over a period of 15 minutes. The mixture was stirred at ambient temperature for 2.25 hours and then at reflux for one hour. Th... | C=C(CC)C(=O)c1ccc(OCC(=O)NCC(=O)O)c(Cl)c1Cl | null | null | null |
24,822 | ord_dataset-fcf7c02bbb814fe696760b5fbfee16bb | null | 1977-01-01T00:05:00 | true | [NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10]C)[C:5]([Cl:12])=[C:4]([Cl:13])[N:3]=1.N[C:15]1N=C(NCCCC)C(Cl)=C(Cl)N=1>>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]([CH3:10])[CH3:15])[C:5]([Cl:12])=[C:4]([Cl:13])[N:3]=1 | CCCNc1nc(N)nc(Cl)c1Cl | CCCCNc1nc(N)nc(Cl)c1Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | In analogous manner to that described in Example 3, 2-amino-4-n-propylamino-5,6-dichloro-pyrimidine and 2-amino-4-n-butylamino-5,6-dichloro-pyrimidine may be produced. Isolation and purification may be effected in conventional manner. | CC(C)Nc1nc(N)nc(Cl)c1Cl | null | null | null |
1,141,258 | ord_dataset-68715347640045adb1b09e6a04722b0e | null | 2012-01-01T00:03:00 | true | [CH3:1][C:2]1[C:3](=[O:28])[O:4][CH:5]([CH2:7][O:8][C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=1.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]([OH:28])[O:4][CH:5]([CH2:7][O:8][C:9]([C:22]2[CH:27]=[CH:26... | CC1=CC(COC(c2ccccc2)(c2ccccc2)c2ccccc2)OC1=O | null | null | CC(C)C[AlH]CC(C)C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1 | null | null | null | null | null | null | null | null | null | null | -78 | 2 | To a solution of 3-methyl-5-trityloxymethyl-5H-furan-2-one (1.85 g, 5 mmol, prepared by the method of Lopez-Herrera et. al., J. Carbohydrate Chem. 1994, 13, 767) in toluene (25 mL) under N2 atmosphere at −78° C. was added dropwise with stirring DiBAL (10 mL, 10 mmol, 1M solution in toluene). The addition rate was maint... | CC1=CC(COC(c2ccccc2)(c2ccccc2)c2ccccc2)OC1O | null | 88 | null |
733,167 | ord_dataset-76dd1b78ee414d2da0ed30700ef026f7 | null | 2006-01-01T00:10:00 | true | [C:1]1([CH2:7][CH2:8][CH:9]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:11]1([NH:17][OH:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.CC1C=CC(S(O)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[CH:11]1([N+:17]([O-:18])=[CH:9][CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1 | ONC1CCCCC1 | O=CCCc1ccccc1 | null | Cc1ccc(S(=O)(=O)O)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)Cl | null | null | null | null | null | null | null | null | null | null | null | null | To a mixture of 3-phenylpropionaldehyde (5.0 g, 37.3 mmol, 1.0 equiv.) and CHCl3 (150 ml) was added N-cyclohexylhydroxylamine (4.30 g, 41.0 mmol, 1.1 equiv) and p-TsOH (few crystals) and the resulting mixture was refluxed under nitrogen for 22 h. Removal of the solvent an oil was obtained which was purified by flash ch... | [O-][N+](=CCCc1ccccc1)C1CCCCC1 | null | 74.3 | null |
961,459 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | [O:1]=[C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][NH:3]1.[H-].[Na+].[CH2:14](I)[CH3:15].O>CN(C=O)C>[CH2:14]([N:3]1[CH:4]=[C:5]([C:8]([O:10][CH3:11])=[O:9])[CH:6]=[CH:7][C:2]1=[O:1])[CH3:15] | CCI | COC(=O)c1ccc(=O)[nH]c1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CN(C)C=O | null | null | null | null | null | null | null | null | null | 25 | 2 | Methyl 2-oxo-1,2-dihydropyridine-5-carboxylate (400 mg, 2.61 mmol) obtained in Step 3 was dissolved in DMF (3 mL), and 55% sodium hydride (125 mg, 2.87 mmol) and ethyl iodide (0.230 mL, 2.87 mmol) were added thereto, followed by stirring at room temperature for 2 hours. Water was added to the reaction mixture, followed... | CCn1cc(C(=O)OC)ccc1=O | null | 79.3 | null |
859,260 | ord_dataset-93908aaae836460ebd48d733eccad483 | null | 2009-01-01T00:01:00 | true | [NH2:1][CH2:2][CH2:3][C:4]1([CH:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[O:9][C:8](=[O:10])[CH2:7][C:6](=[O:11])[CH2:5]1.[O:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[CH2:22][CH2:23][C:24](O)=[O:25].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH:12]1([C:4]2([CH2:3][CH2:2][NH:1][C:24](=[O:25])[CH2:23][CH2:22]... | NCCC1(C2CCCC2)CC(=O)CC(=O)O1 | O=C(O)CCc1ccco1 | null | CN(C)C(On1nnc2cccnc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | null | null | null | null | null | null | null | null | null | null | null | null | A solution of 6-(2-Amino-ethyl)-6-cyclopentyl-dihydro-pyran-2,4-dione (90 mg, 0.4 mmol) from Step 5 below, TEA (0.22 mL, 1.6 mmol), 3-furan-2-yl-propionic acid (67 mg, 0.48 mmol) and HATU (182 mg, 0.48 mmol) in DMF (2 mL) was stirred at room temperature overnight. The reaction was purified directly by preparatory HPLC ... | O=C1CC(=O)OC(CCNC(=O)CCc2ccco2)(C2CCCC2)C1 | null | 18.7 | null |
840,796 | ord_dataset-074f86301ec5441ab3b52d902ac06949 | null | 2008-01-01T00:09:00 | true | [CH:1]1([CH2:7][N:8]2[C:12]([C:13]3[S:14][C:15]4[N:16]=[CH:17][N:18]=[C:19](SC)[C:20]=4[N:21]=3)=[C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:10]=[CH:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([N:32]1C(C2SC3N=CN=C(SC)C=3C=2)=C(C2C=CC=CC=2)N=C1)C.N>>[CH:1]1([CH2:7][N:8]2[C:12]([C:13]3[S:14][C:15]4[N:16]=[CH:... | CCn1cnc(-c2ccccc2)c1-c1cc2c(SC)ncnc2s1 | CSc1ncnc2sc(-c3c(-c4ccccc4)ncn3CC3CCCCC3)nc12 | null | N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared by a similar process to that described for Example 56 but using 2-[1-(cyclohexylmethyl)-4-phenyl-1H-imidazol-5-yl]-7-(methylthio)[1,3]-thiazolo[5,4-d]pyrimidine (Intermediate 79) in place of 6-(1-ethyl-4-phenyl-1H-imidazol-5-yl)-4-(methylthio)thieno[2,3-d]pyrimidine (Intermediate 70) and... | Nc1ncnc2sc(-c3c(-c4ccccc4)ncn3CC3CCCCC3)nc12 | null | null | null |
1,663,277 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [CH3:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][CH2:7][C:8]2[S:9][C:10]3[N:11]=[C:12]([NH2:23])[N:13]=[C:14]([N:17]4[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]4)[C:15]=3[N:16]=2)=[CH:4][CH:3]=1.[Br:26][C:27]1[CH:37]=[CH:36][C:30]([O:31][CH2:32][C:33](O)=[O:34])=[CH:29][CH:28]=1>>[NH2:23][C:12]1[N:13]=[C:14]([N:17]2[CH2:18][CH2:1... | O=C(O)COc1ccc(Br)cc1 | Cc1ccc(CCc2nc3c(N4CCNCC4)nc(N)nc3s2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | This compound was prepared from 2-(4-methylphenethyl)-7-(piperazin-1-yl)thiazolo[5,4-d]pyrimidin-5-amine using 4-bromophenoxyacetic acid in a yield of 47%, according to the procedure for the synthesis of example 50. | Cc1ccc(CCc2nc3c(N4CCN(C(=O)COc5ccc(Br)cc5)CC4)nc(N)nc3s2)cc1 | null | 47 | null |
1,685,157 | ord_dataset-3953983e052a4076aa7cc0880b79cb8b | null | 2016-01-01T00:01:00 | true | C(S[C:4]1[NH:5][C:6](=[O:13])[C:7]2[S:12][CH2:11][CH2:10][C:8]=2[N:9]=1)C.Cl.CC(O)=[O:17]>O>[NH:9]1[C:8]2[CH2:10][CH2:11][S:12][C:7]=2[C:6](=[O:13])[NH:5][C:4]1=[O:17] | CC(=O)O | CCSc1nc2c(c(=O)[nH]1)SCC2 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | null | null | null | null | null | null | null | null | null | null | 110 | null | To a suspension of 2-(ethylthio)-6,7-dihydrothieno[3,2-d]pyrimidin-4(3H)-one (2.80 g, 13.06 mmol) in water (2.0 mL) was added 2.0 mL of conc. HCl and 4.0 mL of AcOH. The mixture was heated at 110° C. overnight. The reaction was cooled and the solid that formed collected by filtration washed with water and methanol, and... | O=c1[nH]c2c(c(=O)[nH]1)SCC2 | null | 82 | null |
590,587 | ord_dataset-7a74d48eeefd45aba53e7258f3ae067a | null | 2003-01-01T00:04:00 | true | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.Br[C:10]([CH2:20][CH3:21])([CH2:18][CH3:19])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].BrN1C(=O)CCC1=O.BrBr>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:10]([CH2:18][CH3:19])([CH2:20][CH3:21])[C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])=[CH:4][CH... | CCC(Br)(CC)C(=O)OC(C)(C)C | Sc1ccc(Br)cc1 | null | BrBr | O=C1CCC(=O)N1Br | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | The synthesis was carried out similarly to Example II-1 from 4-bromothiophenol and 1,1-dimethylethyl 2-bromo-2-ethyl-butanoate [preparation, for example, similarly to Liebigs Ann. Chem. 725, 106-115 (1969); J. Am. Chem. Soc. 77, 946-947 (1955), and bromination with N-bromosuccinimide or bromine, for example similarly t... | CCC(CC)(Sc1ccc(Br)cc1)C(=O)OC(C)(C)C | null | null | null |
1,754,382 | ord_dataset-97eb2ab57fec4160922caae33b54d956 | null | 2016-01-01T00:08:00 | true | [C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21](Br)[CH:20]=2)=[O:16])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:30][N:31](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=... | CC(C)(C)OC(=O)NC1CCN(C(=O)OCc2cc(Br)cc(C(F)(F)F)c2)CC1 | CN(C)C=O | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | [C-]#N | [Zn+2] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | 150 | null | 3-Bromo-5-(trifluoromethyl)benzyl 4-((tert-butoxycarbonyl)amino)piperidine-1-carboxylate (Example 63, step 2) (214 mg, 0.445 mmol), zinc cyanide (26.1 mg, 0.222 mmol) and Pd(PPh3)4 (20.5 mg, 0.018 mmol) were dissolved in DMF (4 ml) and the vial flushed with nitrogen. The mixture was heated in the microwave at 150° C. f... | CC(C)(C)OC(=O)NC1CCN(C(=O)OCc2cc(C#N)cc(C(F)(F)F)c2)CC1 | null | null | null |
620,346 | ord_dataset-2952e63264f5422a84e12cca1e0541ee | null | 2003-01-01T00:12:00 | true | [C:1]([N:9]1[C@@H:13]([CH3:14])[C:12](=[O:15])OC1=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]1([CH3:26])[CH:22]=[CH:21][C:20]([C@@H:23]([NH2:25])[CH3:24])=[CH:19][CH:18]=1.CN1CCOCC1.Cl>C(OCC)(=O)C>[C:17]1([CH3:26])[CH:22]=[CH:21][C:20]([C@@H:23]([NH:25][C:12](=[O:15])[C@H:13]([CH3:14])[NH:9][C:1](=[O:8])[... | C[C@H]1C(=O)OC(=O)N1C(=O)c1ccccc1 | Cc1ccc([C@H](C)N)cc1 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN1CCOCC1 | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | 0.5 | (S)-3-Benzoyl-4-methyl-2,5-oxazolidinedione (N-benzoyl-L-alanine-NCA) (110 mg, 0.50 mmol) was dissolved in ethyl acetate (2.5 mL), followed by the addition of a solution of (S)-1-(p-tolyl)ethylamine (68 mg, 0.50 mmol) in ethyl acetate (2.5 mL) at 0° C. A solution of N-methylmorpholine (61 mg, 0.6 mmol) in ethyl acetate... | Cc1ccc([C@H](C)NC(=O)[C@H](C)NC(=O)c2ccccc2)cc1 | null | 96 | null |
920,157 | ord_dataset-8e59bd24817446f7b1c68e805b8e5f1d | null | 2009-01-01T00:11:00 | true | C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([OH:14])[CH2:9]1)=O)(C)(C)C.[NH2:15][C:16]1[C:25]2[C:20](=[CH:21][C:22](O)=[CH:23][CH:24]=2)[CH:19]=[CH:18][N:17]=1>>[NH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([O:14][C:22]2[CH:21]=[C:20]3[C:25](=[CH:24][CH:23]=2)[C:16]([NH2:15])=[N:17][CH:18]=[CH:19]3)[CH2:9]1 | CC(C)(C)OC(=O)N1CCCC(O)C1 | Nc1nccc2cc(O)ccc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | This compound was prepared from racemic 3-hydroxypiperidine-1-carboxylic acid tert-butyl ester (207 mg, 1.02 mmol) and 1-amino-6-hydroxyisoquinoline (198 mg, 1.23 mmol) by the Mitsunobu procedure described in 3C, subsequent Boc deprotection according to procedure described in 3D gave racemic 6-(piperidin-3-yloxy)-isoqu... | Nc1nccc2cc(OC3CCCNC3)ccc12 | null | 12.1 | null |
1,250,927 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | CS(O[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=1)(=O)=O.[CH:15]1([SH:20])[CH2:19][CH2:18][CH2:17][CH2:16]1>>[Br:14][C:11]1[CH:10]=[CH:9][C:8]([CH2:7][CH2:6][S:20][CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:13][CH:12]=1 | SC1CCCC1 | CS(=O)(=O)OCCc1ccc(Br)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Obtained by working as in Example 1a, starting with 2-(4-bromophenyl)ethyl methanesulfonate (Carbohydr. Res. (2003) 338, 29) and cyclopentanethiol. | Brc1ccc(CCSC2CCCC2)cc1 | null | null | null |
1,722,115 | ord_dataset-36057d699ac5449e9c37eb99abf78b03 | null | 2016-01-01T00:05:00 | true | [Si]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH2:15][C:14]([F:19])([F:18])[CH2:13]1)(C(C)(C)C)(C)C>C1COCC1>[F:19][C:14]1([F:18])[CH2:15][CH2:16][CH2:17][N:12]([CH2:11][CH2:10][CH2:9][OH:8])[CH2:13]1 | CC(C)(C)[Si](C)(C)OCCCN1CCCC(F)(F)C1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 50 | null | To a solution of the product of Step 1 (612 mg) in THF (20 mL) was added HF-TEA (13.58 mL) at room temperature. The solution was heated to 50° C. for 45 minutes. The reaction mixture was concentrated to remove THF and then diluted with ethyl acetate (100 mL) and water was added (100 mL). To that mixture was added Na2CO... | OCCCN1CCCC(F)(F)C1 | null | null | null |
1,420,566 | ord_dataset-f8e6e6a2d2bf4135b9e346456c81700f | null | 2014-01-01T00:04:00 | true | [CH2:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]1[N:13]=[C:12]([NH:14][CH3:15])[N:11]=[C:10]([C:16]2[CH:23]=[C:22]([S:24][CH3:25])[C:19]([C:20]#[N:21])=[C:18](F)[CH:17]=2)[CH:9]=1)[CH3:2].CCN(C(C)C)C(C)C.[NH2:36][NH2:37]>CCO>[CH2:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]1[N:13]=[C:12]([NH:14][CH3:15])[N:11]=[C:10](... | NN | CC[C@@H]1CCCN1c1cc(-c2cc(F)c(C#N)c(SC)c2)nc(NC)n1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 100 | 8 | In a microwave tube, 4-[6-[(2R)-2-ethyl-1-pyrrolidinyl]-2-(methylamino)-4-pyrimidinyl]-2-fluoro-6-(methylthio)benzonitrile (136 mg, 0.366 mmol), 5 mL of EtOH, Hunig's base (0.064 mL, 0.366 mmol), and hydrazine anhydrous (0.069 mL, 2.197 mmol) were added. The yellow suspension mixture was heated to 100° C. in an oil bat... | CC[C@@H]1CCCN1c1cc(-c2cc(SC)c3c(N)n[nH]c3c2)nc(NC)n1 | null | 64.1 | null |
359,999 | ord_dataset-0b24d1f58a024ed7bc2bda95b2430c72 | null | 1997-01-01T00:04:00 | true | [CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([O:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15][NH:16][C:17](=[O:23])[CH2:18][S:19][CH2:20][CH2:21][OH:22])[CH:6]=1)[CH3:3].[C:24](OC(=O)C)(=[O:26])[CH3:25]>>[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([O:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15][NH:16][C:17](=[O:23])[CH2:... | CN(C)Cc1ccnc(OC/C=C\CNC(=O)CSCCO)c1 | CC(=O)OC(C)=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Following a procedure similar to that described in Example 67(c), but using N-[4-(4-dimethylaminomethyl-2-pyridyloxy)-cis-2-butenyl]-2-(2-hydroxyethylthio)acetamide [prepared as described in step (a) above] and acetic anhydride as starting materials, in relative proportions similar to those used in that Example, the ti... | CC(=O)OCCSCC(=O)NC/C=C\COc1cc(CN(C)C)ccn1 | null | 58 | null |
460,735 | ord_dataset-aa5bc55d09b7465ab353e144a7ac3ad1 | null | 2000-01-01T00:03:00 | true | [C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][C:5]1=[O:13])(=[O:3])[CH3:2].[CH2:14]([O:16][C:17](=O)[CH3:18])[CH3:15]>>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[C:14]([O:16][CH2:17][CH3:18])[C:15]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:5]1=[O:13])(=[O:3])[CH3:2] | CCOC(C)=O | CC(=O)N1C(=O)Cc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Yield: about 67% of theory, the product contains about 25 to 34% of 1-acetyl-2-indolinone. Melting point: 123-129° C. (with an amount of 34% of 1-acetyl-2-indolinone). An insoluble fraction is isolated from the above mixture by combining with ethylacetate, extracting with dilute aqueous sodium carbonate solution and wi... | CCOC(=C1C(=O)N(C(C)=O)c2ccccc21)c1ccccc1 | null | null | null |
754,464 | ord_dataset-1b0cd79134f0450eaac8396a4f956c30 | null | 2007-01-01T00:02:00 | true | Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([OH:35])([C:29]2[N:33]([CH3:34])[CH:32]=[N:31][CH:30]=2)[C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]([CH3:20])[C:15](=[O:21])[CH:14]=[C:13]3[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)=[CH:5][CH:4]=1.[CH3:36][CH2:37][O-:38].[Na+].CCO.O>C(O)C>[Cl:28][C:24]1[CH:... | CC[O-] | Cn1cncc1C(O)(c1ccc(CCl)cc1)c1ccc2c(c1)c(-c1cccc(Cl)c1)cc(=O)n2C | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | O | null | null | null | null | null | null | null | null | null | 25 | 18 | A mixture of (±)-6-[[4-(chloromethyl)phenyl]hydroxy(1-methyl-1H-imidazol-5-yl)methyl]-4-(3-chlorophenyl)-1-methyl-2(1H)-quinolinone (0.0002 mol), obtained in Example B14, and EtONa/EtOH (0.0005 mol) in ethanol (1 ml) was stirred at room temperature for 18 hours, poured out into water and extracted with EtOAc. The organ... | CCOCc1ccc(C(O)(c2ccc3c(c2)c(-c2cccc(Cl)c2)cc(=O)n3C)c2cncn2C)cc1 | null | 33.1 | null |
791,539 | ord_dataset-744b04e8228742eb9aa4bde36f5dedf1 | null | 2007-01-01T00:10:00 | true | Cl[C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)[N:8]=2)=[N:4][CH:3]=1.[NH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1>CS(C)=O>[N:26]1([C:2]2[S:6][C:5]([C:7]3[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]4[CH:19]=[C:18](... | C1CNCCN1 | COc1cc(Nc2nccc(-c3ncc(Cl)s3)n2)cc(OC)c1OC | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | null | null | null | null | null | null | null | null | null | null | 100 | null | To solution of [4-(5-Chloro-thiazol-2-yl)-pyrimidin-2-yl]-(3,4,5-trimethoxy-phenyl)-amine (150 mg) in dimethylsulfoxide (2 ml) was added piperazine (300 mg). The mixture was heated to 100° C. for 5 hours then allowed to cool and concentrated under high vacuum to an oil. The residue was purified by HPLC with 0.1% TFA/wa... | COc1cc(Nc2nccc(-c3ncc(N4CCNCC4)s3)n2)cc(OC)c1OC | null | 23.6 | null |
326,677 | ord_dataset-8fe3c7256e6747e59933c880f5f642a0 | null | 1996-01-01T00:03:00 | true | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[S:9](Cl)(=[O:11])=[O:10].C(N(CC)CC)C.[CH2:20]([P:22]([CH2:28][OH:29])(=[O:27])[O:23][CH:24]([CH3:26])[CH3:25])[CH3:21]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:20]([P:22]([CH2:28][O:29][S:9]([C:3]1[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])(=[O:11])=[O:10])(=[O:27])[O:23][C... | O=S(=O)(Cl)c1c(Cl)cccc1Cl | CCP(=O)(CO)OC(C)C | null | CN(C)c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | CCN(CC)CC | null | null | null | null | null | null | null | null | null | 25 | 8 | A solution of 19.6 g of 2,6-dichlorobenzenesulfonyl chloride dissolved in 70 ml of methylene chloride was added dropwise over 40 minutes to a mixture of 25 ml of methylene chloride, 15.0 ml of triethylamine, 1.0 g of DMAP, and 16.5 g of O-isopropyl P-ethyl(hydroxymethyl)phosphinate, (Example 22, Method A). The addition... | CCP(=O)(COS(=O)(=O)c1c(Cl)cccc1Cl)OC(C)C | null | 65.4 | null |
1,663,779 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [CH2:1]([O:8][C@@:9]1([C:36]([F:39])([F:38])[F:37])[CH2:33][C@H:13]2[CH2:14][CH2:15][CH2:16][C:17]3[C:18](=[CH:19][C:20]4[CH:21]=[N:22][N:23]([C:26]5[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=5)[C:24]=4[CH:25]=3)[C@:12]2([CH2:34][NH2:35])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:40][S:41](Cl)(=[... | NC[C@@]12CC[C@](OCc3ccccc3)(C(F)(F)F)C[C@H]1CCCc1cc3c(cnn3-c3ccc(F)cc3)cc12 | CS(=O)(=O)Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCl | null | null | null | null | null | null | null | null | null | null | 25 | 0.5 | Crude ((3R,4aR,12bS)-3-(benzyloxy)-9-(4-fluorophenyl)-3-(trifluoromethyl)-1,2,3,4,4a,5,6,7,9,12b-decahydrobenzo[6,7]cyclohepta[1,2-f]indazol-12b-yl)methan amine (34, R1=4-Fluorophenyl, R3=Trifluoromethyl, R4═H, R3=Benzyl) (0.135 mmol) was dissolved in DCM (3 mL) and methanesulfonyl chloride (0.026 mL, 0.334 mmol) and T... | CS(=O)(=O)NC[C@@]12CC[C@](OCc3ccccc3)(C(F)(F)F)C[C@H]1CCCc1cc3c(cnn3-c3ccc(F)cc3)cc12 | null | null | null |
1,258,386 | ord_dataset-266f60b4555945d6afb2d2bdf5fa04e0 | null | 2013-01-01T00:02:00 | true | [Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][CH:18]=1)[NH2:15].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCl>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:15][C:14]2[CH:16]=[CH:17][CH:18]=[C:12]([O:11][CH3:10])[CH:13]=2)=[CH:4][CH:3]=1 | O=Cc1ccc(Cl)cc1 | COc1cccc(N)c1 | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 8 | 4-Chlorobenzaldehyde (3.41 g, 27.5 mmol) was added to a cooled stirred solution of 3-methoxy aniline (3.38 g, 27.5 mmol) in anhydrous dichloromethane (120 ml). Sodium triacetoxy borohydride (8.16 g, 38.5 mmol) and acetic acid (1.57 ml, 27.5 mmol) were added and the reaction stirred under nitrogen at room temperature ov... | COc1cccc(NCc2ccc(Cl)cc2)c1 | null | 64.6 | null |
526,625 | ord_dataset-293186f5c9b441cab57f03cd3a18ac26 | null | 2001-01-01T00:11:00 | true | [CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[C:8](O)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[NH2:52][C:53]1[S:54][CH:55]=[N:56][N:57]=1>CN(C)C=O>[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C... | Nc1nncs1 | O=C(O)C(CC1CCCC1)c1ccc(Cl)c(Cl)c1 | null | CN(C)C(On1nnc2ccccc21)=[N+](C)C | F[P-](F)(F)(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CN(C)C=O | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | null | null | A solution of 3-cyclopentyl-2-(3,4-dichlorophenyl)-propionic acid (prepared from Example 38, 200.0 mg, 0.70 mmol), O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (316.9 mg, 0.84 mmol), N,N-diisopropylethylamine (365 mL, 2.09 mmol), and 2-amino-1,3,4-thiadiazole (140.8 mg, 1.39 mmol) in dry N,N-dim... | O=C(Nc1nncs1)C(CC1CCCC1)c1ccc(Cl)c(Cl)c1 | null | 76.1 | null |
Subsets and Splits
No community queries yet
The top public SQL queries from the community will appear here once available.