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 ⌀ |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
1,161,175 | ord_dataset-d24cc23b3db94284bb83a2ccdd9eb880 | null | 2012-01-01T00:05:00 | true | [CH3:1][C:2]1([CH3:16])[CH2:7][O:6][CH:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:4][C@H:3]1[CH:14]=[CH2:15].[H-].C([Al+]CC(C)C)C(C)C>ClCCl>[CH3:1][C:2]([CH3:16])([C@@H:3]([O:4][CH2:5][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH:14]=[CH2:15])[CH2:7][OH:6] | C=C[C@@H]1OC(c2ccccc2)OCC1(C)C | null | null | CC(C)C[Al+]CC(C)C | [H-] | 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 | Following the general procedure for the reductive ring opening of benzylidene-type acetals of 1,3-diols of Description 9, 9.5 g (43.5 mmol) of (4S)-5,5-dimethyl-2-phenyl-4-vinyl-1,3-dioxane (7c) was reacted with 25.0 mL (19.9 g, 140.0 mmol) of diisobutylaluminum hydride [(iBu)2AlH, DIBAL(H)] in 150 mL of anhydrous dich... | C=C[C@H](OCc1ccccc1)C(C)(C)CO | null | 87.7 | null |
483,391 | ord_dataset-cb5c1a9eddff4790b1bd650617c32d34 | null | 2000-01-01T00:11:00 | true | Br[C:2]1[C:7]([C:8]#[N:9])=[C:6]([NH2:10])[CH:5]=[C:4]([NH2:11])[N:3]=1.CC([O-])=O.[K+]>O1CCCC1.CO.[Pd]>[C:8]([C:7]1[CH:2]=[N:3][C:4]([NH2:11])=[CH:5][C:6]=1[NH2:10])#[N:9] | N#Cc1c(N)cc(N)nc1Br | null | null | [Pd] | CC(=O)[O-] | [K+] | 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 | null | null | A solution of (II) (15.1 g, 0.071 mol), KOAc (7.0 g, 0.071 mol) and 5% Pd/C (4 g) in THF (tetrahydrofuran) (130 mL) and MeOH (methanol) (70 mL) was hydrogenated (55 psi/20° C.) for 7 days. The resulting solution was filtered over Celite, washing with THF/MeOH, then the solvents were removed under reduced pressure. The ... | N#Cc1cnc(N)cc1N | null | 69.1 | null |
59,350 | ord_dataset-28b19b59e93c47698a5a2b21048ec201 | null | 1979-01-01T00:10:00 | true | CCOCC.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([S:22][C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)=[C:17]([CH:21]=1)[C:18](O)=[O:19]>O>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([S:22][C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)=[C:17]([CH:21]=1)[CH2:18][OH:19] | O=C(O)c1cc(Cl)ccc1Sc1cccs1 | null | null | [Al+3] | [H-] | [Li+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCOCC | null | null | null | null | null | null | null | null | null | null | null | To 30 ml of abs. ether cooled to 3° is added under nitrogen 1.14 g (0.03 mole) of lithium aluminium hydride, and there is then added dropwise at 5°-10° with stirring, within half an hour, a solution of 5.4 g (0.02 mole) of 5-chloro-2-(2-thienylthio)-benzoic acid (produced according to Swiss Patent Specification No. 405... | OCc1cc(Cl)ccc1Sc1cccs1 | null | null | null |
584,672 | ord_dataset-cb5dd7a8b94e4f19a9148a1904b0dcb6 | null | 2003-01-01T00:03:00 | true | [CH3:1][O:2][CH2:3][O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([O:20]C)=[O:19])=[CH:14][CH:13]=2)=[CH:7][C:6]=1[CH3:22].[OH-].[Na+]>>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([OH:20])=[O:19])=[CH:14][CH:13]=2)=[CH:7][C:6]=1[CH3:22] | COCOc1c(C)cc(-c2ccc(C(=O)OC)cc2)cc1C | null | null | [Na+] | [OH-] | 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 similar manner to that described in Example 2, a reaction was carried out using methyl 4′-methoxymethoxy-3′,5′-dimethylbiphenyl-4-carboxylate (1.24 g) and aqueous sodium hydroxide (1N, 8.20 ml) and the reaction mixture was treated to afford the desired compound (0.99 g) as colorless crystals. | COCOc1c(C)cc(-c2ccc(C(=O)O)cc2)cc1C | null | 83.7 | null |
646,246 | ord_dataset-c975a50a7600448fabd558f4a94a3e29 | null | 2004-01-01T00:08:00 | true | [CH2:1]([N:3]([CH2:29][CH3:30])[C:4](=[O:28])[C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:18]2[CH:19]=[CH:20][CH:21]=[C:22]3[C:27]=2[N:26]=[CH:25][CH:24]=[CH:23]3)[N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:7][CH:6]=1)[CH3:2].CCN(CC)CC.[CH3:38][C:39]1[CH:46]=[CH:45][C:42]([CH2:43]Br)=[CH:41][CH:40]=1>C(Cl)Cl>[CH2:29](... | Cc1ccc(CBr)cc1 | CCN(CC)C(=O)c1ccc(C(c2cccc3cccnc23)N2CCNCC2)cc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCN(CC)CC | ClCCl | null | null | null | null | null | null | null | null | null | null | 8 | To a solution of compound 1 (0.80 g; 1.99 mmol) in CH2Cl2 (20 ml) was added Et3N (0.83 ml; 5.97 mmol) followed by p-methyl benzyl bromide (773 mg; 4.18 mmol). The reaction mixture was stirred overnight and was then was concentrated under reduced pressure. Purification by reverse phase using 10%-30% CH3CN/H2O. | CCN(CC)C(=O)c1ccc(C(c2cccc3cccnc23)N2CCN(Cc3ccc(C)cc3)CC2)cc1 | null | null | null |
78,557 | ord_dataset-0c37e633e9814a6e886187796cacf216 | null | 1981-01-01T00:03:00 | true | [OH:1][CH:2]([CH:4]1[C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]=2[S:7][CH2:6][CH2:5]1)[CH3:3].C(OC(=O)C)(=O)C.[OH-].[NH4+]>CS(C)=O>[C:2]([CH:4]1[C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]=2[S:7][CH2:6][CH2:5]1)(=[O:1])[CH3:3] | CC(O)C1CCSc2[nH]c3ccccc3c21 | null | null | [NH4+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)OC(C)=O | CS(C)=O | null | null | null | null | null | null | null | null | null | 25 | 20 | To a solution of the product (300 mg) of the above (1) in dimethylsulfoxide (5 ml) is added acetic anhydride (0.7 ml). The mixture is stirred at room temperature for 20 hours. The reaction mixture is poured into ice water, made alkaline with ammonium hydroxide and extracted with ether. The extract is washed with water,... | CC(=O)C1CCSc2[nH]c3ccccc3c21 | null | null | null |
745,051 | ord_dataset-4b705442211b4a3988e26d5f65098160 | null | 2006-01-01T00:12:00 | true | C[CH:2]([CH:6]1[C:11]2=[CH:12][C:13]3[C:18]([N:10]2[CH2:9][CH2:8][CH2:7]1)=[CH:17][C:16]([F:19])=[CH:15][C:14]=3[CH:20]([CH3:22])[CH3:21])[C:3]([O-:5])=[O:4].[CH:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][C:24]=1[C:33](Cl)=[O:34]>>[F:19][C:16]1[CH:17]=[C:18]2[C:13]([C:12]([C:33]([C:24]3[CH:25]=[... | O=C(Cl)c1ccc2ccccc2c1 | CC(C)c1cc(F)cc2c1cc1n2CCCC1C(C)C(=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 | Starting from (+/−)-methyl(3-fluoro-1-isopropyl-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl)acetate (Example 122, Step 4) and 2-naphthoyl chloride, the title compound was synthesized following the procedures described in Step 1 of Example 61 and Step 10 of Example 7. | CC(C)c1cc(F)cc2c1c(C(=O)c1ccc3ccccc3c1)c1n2CCCC1CC(=O)O | null | null | null |
1,209,463 | ord_dataset-fb72428f30234761b4216139dc228d0c | null | 2012-01-01T00:09:00 | true | BrC1C=CC2C3C=CC(C(=O)COC([CH:18]4[CH2:24][C:21]5([CH2:23][CH2:22]5)[CH2:20][N:19]4[C:25]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:26])=O)=CC=3OC=2C=1.C([O-])(=O)C.[NH4+]>C1(C)C(C)=CC=CC=1>[CH2:28]([O:27][C:25]([N:19]1[CH2:18][CH2:24][C:21]2([CH2:23][CH2:22]2)[CH2:20]1)=[O:26])[C:29]1[CH:30]=[CH:... | O=C(COC(=O)C1CC2(CC2)CN1C(=O)OCc1ccccc1)c1ccc2c(c1)oc1cc(Br)ccc12 | null | null | CC(=O)[O-] | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1C | null | null | null | null | null | null | null | null | null | null | null | null | To the solution of (s) 5-aza-spiro[2.4]heptane-5,6-dicarboxylic acid 5-benzyl ester (138 mg, 0.5 mmol) and triethylamine (65 μl, 0.47 mmol) in acetonitrile (3 ml) was added slowly a solution of 2-bromo-1-(7-bromo-dibenzofuran-3-yl)-ethanone (143 mg, 0.39 mmol) in DMF (4 ml). The mixture was stirred for 12 hours, and th... | O=C(OCc1ccccc1)N1CCC2(CC2)C1 | null | 166.3 | null |
430,996 | ord_dataset-2d21ceeb77844edc9eaedb2fabca2ff1 | null | 1999-01-01T00:04:00 | true | [CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:22]#[C:23][C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([NH:30]C(=O)C(F)(F)F)[CH:25]=4)[CH2:20][CH2:19][CH2:18][C:17](=[O:21])[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+]>CO.O>[NH2:30][C:26]1[CH:25]=[C:24]([C:23]#[C:22][C:15]2(... | COc1ccc(C2(C#Cc3cccc(NC(=O)C(F)(F)F)c3)CCCC(=O)C2)cc1OC1CCCC1 | null | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CO | null | null | null | null | null | null | null | null | null | null | 18 | To a solution of 3-(3-cyclopentyloxy4-methoxyphenyl)-3-(3-trifluoroacetamidophenylethynyl)cyclohexan-1-one (0.62 g, 1.24 mmol) in 95:5 methanol/water (10 mL) under an argon atmosphere was added potassium carbonate (0.86 g, 6.2 mmol). The mixture was refluxed for 6 h and was stired for 18 h at room temperature. The soli... | COc1ccc(C2(C#Cc3cccc(N)c3)CCCC(=O)C2)cc1OC1CCCC1 | null | 77.9 | null |
1,095,248 | ord_dataset-af85e6f81c2d49f08086afd6d9e6959c | null | 2011-01-01T00:10:00 | true | C([O:3][C:4]([C:6]1[N:7]=[CH:8][N:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]3[C:18]([Cl:23])=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:12]=2)[CH:10]=1)=[O:5])C.[OH-].[K+]>C(O)C>[Cl:23][C:18]1[C:17]([C:13]2[CH:12]=[C:11]([N:9]3[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=[CH:8]3)[CH:16]=[CH:15][CH:14]=2)=[CH:22][CH:21]=[CH:20][... | CCOC(=O)c1cn(-c2cccc(-c3cccnc3Cl)c2)cn1 | null | null | [K+] | [OH-] | 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 | This compound is prepared by hydrolysis of 9l using a 1:1 mixture of aqueous potassium hydroxide (2M) and ethanol. | O=C(O)c1cn(-c2cccc(-c3cccnc3Cl)c2)cn1 | null | null | null |
1,249,699 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [N:1]([CH2:4][CH2:5][C@@H:6]1[O:10][C:9]([CH3:12])([CH3:11])[O:8][C:7]1([CH3:14])[CH3:13])=[N+]=[N-]>C(OCC)(=O)C.O=[Pt]=O>[CH3:11][C:9]1([CH3:12])[O:10][C@@H:6]([CH2:5][CH2:4][NH2:1])[C:7]([CH3:14])([CH3:13])[O:8]1 | CC1(C)O[C@@H](CCN=[N+]=[N-])C(C)(C)O1 | null | null | O=[Pt]=O | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | 18 | Step I A suspension of (S)-5-(2-azido-ethyl)-2,2,4,4-tetramethyl-[1,3]dioxolane (1.6 g, 8 mmol) and PtO2 (0.32 g) in ethyl acetate (15 mL) was vigorously shaken in a Parr under atmosphere of H2 (50 psi) for 18 h. The mixture was filtered through a short pad of celite. The filtrate was concentrated to give 2-((S)-2,2,5,... | CC1(C)O[C@@H](CCN)C(C)(C)O1 | null | 93.8 | null |
1,034,907 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | [CH3:1][C:2]1[N:3]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:4]2[C:13]3[CH:12]=[CH:11][C:10]([OH:14])=[CH:9][C:8]=3[N:7]=[CH:6][C:5]=2[N:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:39]1[CH:43]=[CH:42][C:41]([CH2:44]O)=[CH:40]1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[O:39]1[CH:43]=[CH:42][C:41]([CH2:44][O:14][C:10]2[CH:11]=... | Cc1nc2cnc3cc(O)ccc3c2n1CC(C)C | OCc1ccoc1 | null | CC(C)OC(=O)N=NC(=O)OC(C)C | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | 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 | 144 | 2-Methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-ol (300 mg, 1.17 mmol), triphenylphosphine (921 mg, 3.51 mmol), and 3-furanmethanol (173 mg, 1.76 mmol) were slurried in 20 mL of anhydrous THF. After 5 minutes diisopropyl azodicarboxylate (710 mg, 3.51 mmol) was added dropwise to the mixture. The resulting homog... | Cc1nc2cnc3cc(OCc4ccoc4)ccc3c2n1CC(C)C | null | 127.4 | null |
357,625 | ord_dataset-58ec5adfcd8648dc9e26ee757d289517 | null | 1997-01-01T00:03:00 | true | [CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][Si](C(C)(C)C)(C)C)[CH2:9][C@H:8]1[CH2:20][CH2:21][OH:22])=[O:6])[CH:2]=[CH2:3].Cl.C[O-].[Na+]>CO.ClCCl>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([OH:12])[CH2:9][C@H:8]1[CH2:20][CH2:21][OH:22])=[O:6])[CH:2]=[CH2:3] | C=CCOC(=O)N1C[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1CCO | null | null | C[O-] | Cl | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 1 | A solution of (2R,4R)-1-allyloxycarbonyl-4-(t-butyldimethylsilyloxy)-2-(2-hydroxyethyl)pyrrolidine (5.0 g) and conc. hydrochloric acid (2.53 ml) in methanol (25 ml) was stirred under ice-cooling for 10 minutes and then stirred at ambient temperature for 1 hour. To the reaction mixture cooled at 0° C. was added 28% sodi... | C=CCOC(=O)N1C[C@H](O)C[C@H]1CCO | null | 94.9 | null |
1,566,436 | ord_dataset-4e54080057a44c3887653391e24c90b6 | null | 2015-01-01T00:03:00 | true | Cl[C:2]1[N:3]=[C:4]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[C:5]2[S:10][C:9]([CH2:11][N:12]3[CH2:17][CH2:16][N:15]([C:18](=[O:22])[CH:19]([OH:21])[CH3:20])[CH2:14][CH2:13]3)=[C:8]([CH3:23])[C:6]=2[N:7]=1.[CH3:30][C:31]1[C:36](B2OC(C)(C)C(C)(C)O2)=[CH:35][N:34]=[C:33]([NH2:46])[N:32]=1>>[NH2:46][C:33]1[N:32]=[C:... | Cc1c(CN2CCN(C(=O)C(C)O)CC2)sc2c(N3CCOCC3)nc(Cl)nc12 | Cc1nc(N)ncc1B1OC(C)(C)C(C)(C)O1 | 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 | 1-[4-(2-Chloro-7-methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-piperazin-1-yl]-2-hydroxy-propan-1-one (200 mg) was coupled to 4-methyl-5-(4,4,5,5-tetramethyl (1,3,2-dioxaborolan-2-yl))pyrimidine-2-ylamine via General Procedure A to yield 20 mg of 349. MS (Q1) 513.2 (M)+. | Cc1nc(N)ncc1-c1nc(N2CCOCC2)c2sc(CN3CCN(C(=O)[C@H](C)O)CC3)c(C)c2n1 | null | null | null |
1,657,121 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [N:1]([CH2:4][C@@H:5]1[O:10][CH2:9][C@@H:8]([N:11]2[C:15]3=[C:16]4[S:22][CH:21]=[CH:20][C:17]4=[N:18][CH:19]=[C:14]3[N:13]=[C:12]2[C@H:23]([OH:25])[CH3:24])[CH2:7][CH2:6]1)=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][C@@H:5]1[O:10][CH2:9][C@@H:8]([N:11]2[C:15]3=[C:16]4[S:22][CH:21]=[CH:20][C:17]4=[N:18][CH:19]=[C:14]3[N:13]=[C:12... | C[C@@H](O)c1nc2cnc3ccsc3c2n1[C@H]1CC[C@H](CN=[N+]=[N-])OC1 | 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 | A solution of (1R)-1-{1-[(3S,6R)-6-(azidomethyl)tetrahydro-2H-pyran-3-yl]-1H-imidazo[4,5-d]thieno[3,2-b]pyridin-2-yl}ethanol (12 mg, 0.034 mmol) in methanol (0.2 mL) was added 10% palladium on carbon (5.7 mg). The resulting mixture was stirred under H2 balloon overnight. The reaction mixture was filtered through a pad ... | C[C@@H](O)c1nc2cnc3ccsc3c2n1[C@H]1CC[C@H](CN)OC1 | null | 97.3 | null |
110,978 | ord_dataset-ac04cf1ba5724e9b93d39b77e9740b21 | null | 1983-01-01T00:11:00 | true | [C:1]([OH:8])(=[O:7])[CH:2]=[CH:3][CH2:4][CH2:5][CH3:6].[CH3:9][S:10][CH2:11]Cl.C(N(CC)CC)C>>[C:1]([O:8][CH2:9][S:10][CH3:11])(=[O:7])[CH:2]=[CH:3][CH2:4][CH2:5][CH3:6] | CSCCl | CCCC=CC(=O)O | null | null | null | 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 | This product was prepared according to the procedure described in Example 1, by reacting 2-hexenoic acid with chloromethyl methyl sulfide in the presence of one equivalent of triethylamine; b.p. 75°-76° C./2 mm Hg, n20 1.4836. | CCCC=CC(=O)OCSC | null | null | null |
733,263 | ord_dataset-76dd1b78ee414d2da0ed30700ef026f7 | null | 2006-01-01T00:10:00 | true | [CH2:1]([O:3][C:4](=[O:17])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH3:16])([CH3:7])[CH3:6])[CH3:2].Cl[CH2:19][C:20]1[C:21]([CH2:36][O:37][CH3:38])=[N:22][C:23]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=2)=[CH:24][CH:25]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[CH2:1... | COCc1nc(-c2ccc(C(F)(F)F)cc2)ccc1CCl | CCOC(=O)C(C)(C)Oc1ccc(O)cc1C | null | O=C([O-])[O-] | [Cs+] | 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 | 25 | 22 | To 0.097 g (0.407 mmol) of 2-(4-hydroxy-2-methyl-phenoxy)-2-methyl-propionic acid ethyl ester (described in WO 02/092590) and 0.145 g (0.459 mmol) of the above prepared 3-chloromethyl-2-methoxymethyl-6-(4-trifluoromethyl-phenyl)-pyridine, dissolved in 2.5 ml of abs. acetonitrile, was added 0.180 g of Cs2CO3 (0.552 mmol... | CCOC(=O)C(C)(C)Oc1ccc(OCc2ccc(-c3ccc(C(F)(F)F)cc3)nc2COC)cc1C | null | null | null |
908,939 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | [Br:1][C:2]1[CH:12]=[C:11]([CH3:13])[C:5]([O:6][CH2:7][C:8]([OH:10])=O)=[C:4]([CH3:14])[CH:3]=1.[NH2:15][C:16]1[CH:17]=[CH:18][C:19]([S:34]([CH2:37][CH3:38])(=[O:36])=[O:35])=[C:20]([CH:33]=1)[CH2:21][NH:22][C:23](=[O:32])[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.O=P(Cl)(Cl)Cl>N1C=CC=CC=1>[Br:1][C:2]... | Cc1cc(Br)cc(C)c1OCC(=O)O | CCS(=O)(=O)c1ccc(N)cc1CNC(=O)OCc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | O=P(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 0.33 | To a solution of 79A (100 mg, 0.386 mmol) and 28A (148 mg, 0.386 mmol) in 2 mL pyridine at −15° C., was added POCl3 (0.040 mL, 0.425 mmol), dropwise. The mixture was stirred at this temperature for 20 min, then was quenched with water. The mixture was diluted with EtOAc, washed with water (2×), 1N HCl, water, sat. NaHC... | CCS(=O)(=O)c1ccc(NC(=O)COc2c(C)cc(Br)cc2C)cc1CNC(=O)OCc1ccccc1 | null | 97.6 | null |
1,540,342 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | Cl[C:2]1[C:3](=[O:11])[N:4]([CH3:10])[N:5]=[CH:6][C:7]=1OC.O.[NH2:13]N>O>[NH2:13][C:2]1[C:3](=[O:11])[N:4]([CH3:10])[N:5]=[CH:6][CH:7]=1 | COc1cnn(C)c(=O)c1Cl | NN | null | null | 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 | 80 | 3 | 9.14 g (52 mmoles) of intermediate 4b are placed in mL hydrazine monohydrate. The reaction medium is agitated for 3 h at 80° C. then diluted in 100 mL water and extracted with CH2Cl2 then with AcOEt. After drying over Na2SO4, the organic phases are evaporated and the residue obtained is purified by silica gel flash chr... | Cn1nccc(N)c1=O | null | null | null |
262,182 | ord_dataset-ddb1b60bec5c45e9a2938b6dac04376c | null | 1993-01-01T00:02:00 | true | [Cl-].[NH4+].O.[CH3:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[C:10]([N+:27]([O-])=O)[CH:9]=1)(=[O:7])=[O:6]>[Fe].C(O)(C)C>[NH2:27][C:10]1[CH:9]=[C:8]([S:5]([CH3:4])(=[O:6])=[O:7])[CH:13]=[CH:12][C:11]=1[O:14][CH2:15][CH2:... | CCCCCCCCCCCCOc1ccc(S(C)(=O)=O)cc1[N+](=O)[O-] | null | null | [Fe] | [Cl-] | [NH4+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(C)O | O | null | null | null | null | null | null | null | null | null | null | null | A mixture of 25.2 g of iron powder, 1 g of ammonium chloride, 25 ml of water and 250 ml of isopropanol was heated and stirred in a nitrogen stream. To the mixture 23.1 g of dodecyl 4-methylsulfonyl-2-nitrophenyl ether was added. After the conclusion of the addition and a 1-hour stirring, the resulting solution was filt... | CCCCCCCCCCCCOc1ccc(S(C)(=O)=O)cc1N | null | null | null |
133,812 | ord_dataset-34cf5f1378de4e34844aea93a2f9a9d3 | null | 1985-01-01T00:08:00 | true | [Br:1][C:2]1[CH:3]=[C:4]([CH3:13])[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])=[N:6][CH:7]=1.[CH2:14]1[O:32][C:31]2[CH:30]=[CH:29][C:18]([CH2:19][C:20]3[C:21](=[O:28])[NH:22][C:23](SC)=[N:24][CH:25]=3)=[CH:17][C:16]=2[O:15]1>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH3:13])[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:23... | Cc1cc(Br)cnc1CCCCN | CSc1ncc(Cc2ccc3c(c2)OCO3)c(=O)[nH]1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | 5-Bromo-2-(4-aminobutyl)-3-methylpyridine, (0.88 g) and 5-(3,4-methylenedioxybenzyl)-2-methylthio-4-pyrimidone (0.83 g) were refluxed in pyridine (3 ml) for 24 hours. The pyridine was removed in vacuo and the resulting brown oil triturated with ethanol giving a cream solid which was recrystallised from dimethylformamid... | Cc1cc(Br)cnc1CCCCNc1ncc(Cc2ccc3c(c2)OCO3)c(=O)[nH]1 | null | 77.7 | null |
1,589,400 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | [OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[O:11])[O:9][C:8]([CH3:13])([CH3:12])[O:7][C:6]=2[CH:14]=1.CC1C=CC(S(O[CH2:26][CH2:27][O:28][CH2:29][CH2:30][O:31][CH3:32])(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+]>CC#N.O>[CH3:32][O:31][CH2:30][CH2:29][O:28][CH2:27][CH2:26][O:1][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[O:11])[O:9][C:8]([CH3... | CC1(C)OC(=O)c2ccc(O)cc2O1 | COCCOCCOS(=O)(=O)c1ccc(C)cc1 | null | O=C([O-])[O-] | [K+] | 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 | A solution of 7-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one, (19.4 g, 100 mmol), 2-(2-methoxyethoxy)ethyl 4-methylbenzenesulfonate (27.4 g, 100 mmol) and K2CO3 (41 g, 300 mmol) in CH3CN (500 mL) was refluxed for 4.5 hours. The mixture was poured in H2O (1000 mL) and extracted twice with CH2Cl2 (500 mL). The combi... | COCCOCCOc1ccc2c(c1)OC(C)(C)OC2=O | null | 74.2 | null |
191,617 | ord_dataset-d1bd8c96676b4d21aad27b173c6b4eff | null | 1989-01-01T00:06:00 | true | [H-].[Na+].[CH2:3]1[O:11][C:10]2[CH:9]=[CH:8][C:7]([CH:12]([C:15]([F:18])([F:17])[F:16])[CH2:13][OH:14])=[CH:6][C:5]=2[O:4]1.[O:19]([C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29]Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[O:19]([C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29][O:14][CH2:13... | OCC(c1ccc2c(c1)OCO2)C(F)(F)F | BrCc1cccc(Oc2ccccc2)c1 | null | [H-] | [Na+] | 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 | 14 | Under a nitrogen atmosphere, 0.18 g of sodium hydride (60% oil dispersion) was added to 20 ml of dry THF. A solution of 1.0 g of 2-(3,4-methylenedioxyphenyl)-3,3,3-trifluoropropanol and 1.17 g of 3-phenoxybenzyl bromide in 10 ml of dry THF was then added with ice-cooling, and the reaction solution was stirred at room t... | FC(F)(F)C(COCc1cccc(Oc2ccccc2)c1)c1ccc2c(c1)OCO2 | null | 67.5 | null |
685,097 | ord_dataset-359b8fc87f4244be89d6f02bc5036eac | null | 2005-01-01T00:09:00 | true | [CH3:1][C:2]1[C:14]2[C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][C:5]=2[N:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[N:3]=1.[H-].[Na+].I[CH3:25].[OH-].[Na+]>CN(C)C=O.O>[CH3:1][C:2]1[C:14]2[C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[N:6]([CH3:25])[C:5]=2[N:4]([C:16]2[CH:21]=[C... | CI | Cc1nn(-c2ccccn2)c2[nH]c3ccccc3c(=O)c12 | null | [H-] | [Na+] | [OH-] | 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 | 1 | To an ice-cold solution of 3-methyl-1-(2-pyridinyl)-1,9-dihydro-4H-pyrazolo[3,4-b]quinolin-4-one (1.11 g, 4.0 mmol) in N,N-dimethylformamide (16 mL), sodium hydride (oiliness, content 60%, 0.19 g, 4.8 mmol) was added and the mixture was stirred at room temperature for 1 hour. Subsequently, iodomethane (2.5 mL, 40.2 mmo... | Cc1nn(-c2ccccn2)c2c1c(=O)c1ccccc1n2C | null | 40.5 | null |
868,287 | ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | null | 2009-01-01T00:03:00 | true | [C:1]([C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]3[N:15]([CH:16]=2)[CH:14]=[CH:13][S:12]3)[CH:6]=[CH:7][CH:8]=1)#[N:2].[C:17](OC(=O)C)(=[O:19])[CH3:18].S(=O)(=O)(O)O>ClCCl>[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]3[N:15]([C:16]=2[C:17](=[O:19])[CH3:18])[CH:14]=[CH:13][S:12]3)[CH:6]=[CH:7][CH:8]=1)#[N:2] | N#Cc1cccc(-c2cn3ccsc3n2)c1 | CC(=O)OC(C)=O | null | O=S(=O)(O)O | 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 | 135 | null | To a mixture of 6-(3-cyanophenyl)-imidazo[2,1-b]thiazole (5.50 g, 24.4 mmol) and acetic anhydride (50 mL) was added 0.6 mL of concentrated sulfuric acid. The reaction mixture was heated at 135° C. for 5 hours. After cooling to room temperature, the reaction mixture was diluted with dichloromethane (100 mL), washed with... | CC(=O)c1c(-c2cccc(C#N)c2)nc2sccn12 | null | 74 | null |
1,602,305 | ord_dataset-9cecb3a8d3b9494191b28dcefea66af2 | null | 2015-01-01T00:07:00 | true | [CH2:1]([NH2:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]>[Ni].O>[C:1](#[N:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9] | CCCCCCCCCN | null | null | [Ni] | 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 | 90 | null | 50 g of nonylamine and 50 g of water are introduced into a 750-ml autoclave equipped with a self-aspirating turbine. 5 g of basified Raney nickel doped with 2% by weight of Cr are added. The reactor is flushed with twice 10 bar of nitrogen and then with twice 10 bar of hydrogen. The autoclave is placed under 20 bar of ... | CCCCCCCCC#N | null | 98 | null |
571,453 | ord_dataset-5e1b2445a3d94ea592ddf2c284118a1e | null | 2002-01-01T00:11:00 | true | [C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].Cl[C:13]1[C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=[CH:15][C:14]=1[N+:23]([O-:25])=[O:24]>CS(C)=O>[CH3:22][O:21][C:19]([C:18]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:23]([O-:25])=[O:24])[C:13]=1[CH:2]([C:1]([O:8][CH3:9])=[O:7])[C:3]([O:5][CH3:6... | COC(=O)c1cccc([N+](=O)[O-])c1Cl | COC(=O)CC(=O)OC | null | [H-] | [Na+] | 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 | 1 | Dimethyl malonate (6.0 mL) was added to the ice-cold suspension of 2.1 g of sodium hydride in 16 mL of DMSO. The reaction mixture was then stirred at 100° C. for 1 hour and cooled to room temperature. 2-chloro-3-methoxycarbonyl-nitrobenzene (2.15 g) was added to the above mixture in one portion and the mixture was heat... | COC(=O)c1cccc([N+](=O)[O-])c1C(C(=O)OC)C(=O)OC | null | null | null |
1,507,276 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | [Br:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[N:7][C:8]([Cl:19])=[CH:9][C:10]=3[N+]([O-])=O)[C:5](=[O:20])[C:4]=2[CH:3]=1.[F-:21].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C=O)C>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[N:7][C:8]([Cl:19])=[CH:9][C:10]=3[F:21])[C:5](=[O:20])[C:4]=2[CH:3]=1 | O=c1c2cc(Br)ccc2oc2c([N+](=O)[O-])cc(Cl)nc12 | [F-] | null | CCCC[N+](CCCC)(CCCC)CCCC | null | 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 | 0.25 | To a solution of 8-bromo-2-chloro-4-nitro-10H-chromeno[3,2-b]pyridin-10-one (80 mg, 0.225 mmol) in 0.8 mL of DMF at 0° C. was added tetrabutylammonium fluoride (1M in THF, 0.45 mL, 0.450 mmol) dropwise. After 15 minutes, the reaction was quenched with saturated NH4Cl (20 mL) and extracted with ethyl acetate (2×10 mL). ... | O=c1c2cc(Br)ccc2oc2c(F)cc(Cl)nc12 | null | null | null |
1,457,165 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [CH2:1]([O:3][C:4](=[O:26])[CH2:5][O:6][C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9](B2OC(C)(C)C(C)(C)O2)[CH:8]=1)[CH3:2].[C:27]1(=[O:32])[CH2:31][CH2:30][CH:29]=[CH:28]1>F[B-](F)(F)F>[O:32]=[C:27]1[CH2:31][CH2:30][C@@H:29]([C:9]2[CH:8]=[C:7]([CH:12]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:10]=2)[O:6]... | O=C1C=CCC1 | CCOC(=O)COc1cc(B2OC(C)(C)C(C)(C)O2)cc(C(F)(F)F)c1 | null | F[B-](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 | The title compound was prepared from [3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-5-trifluoromethyl-phenoxy]-acetic acid ethyl ester and 2-cyclopenten-1-one with Rh(R-BINAP)(nbd)]BF4 as catalyst in a manner similar to the one described for Preparation 6. | CCOC(=O)COc1cc([C@@H]2CCC(=O)C2)cc(C(F)(F)F)c1 | null | null | null |
792,586 | ord_dataset-744b04e8228742eb9aa4bde36f5dedf1 | null | 2007-01-01T00:10:00 | true | [NH2:1][C:2]1[N:6]([C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=2)[N:5]=[C:4]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=2[O:24][CH3:25])[N:3]=1.C[Si]([N:30]=[N+:31]=[N-:32])(C)C.C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[CH3:25][O:24][C:17]1[CH:18]=[C:19]([O:22][CH3:23])[CH:20]=[CH:21][C:16]=... | C[Si](C)(C)N=[N+]=[N-] | COc1ccc(Nc2nc(N)n(-c3ccc(C#N)cc3)n2)c(OC)c1 | null | CCCC[Sn](=O)CCCC | 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 | 110 | null | 4-[5-Amino-3-(2,4-dimethoxy-phenylamino)-[1,2,4]triazol-1-yl]-benzonitrile (52 mg, 0.15 mmol) and trimethylsilyl azide (20 mg, 0.165 mol) were suspended in 1 mL toluene with a catalytic amount of di-butyltin oxide and heated to 110° C. for 18 hours. The toluene was evaporated and the residue purified by preparative HPL... | COc1ccc(Nc2nc(N)n(-c3ccc(-c4nnn[nH]4)cc3)n2)c(OC)c1 | null | 22.8 | null |
7,437 | ord_dataset-653be8036d754ce7b8a1c4cd419eaf55 | null | 1976-01-01T00:05:00 | true | C[O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:15])[CH:14]=1)=[CH:11][C:10]1[C:16](=[O:24])[CH:17]=[C:18]([C:20]([O:22]C)=[O:21])[NH:19][C:9]=1[C:8]=2[Cl:25])=[O:4].[OH-].[Na+].Cl>O>[Cl:25][C:8]1[C:7]2[NH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:14][C:13](=[O:15])[C:12]=2[CH:11]=[C:10]2[C:9]=1[NH:19][C:18]([C:20]([OH:22])=[O:... | COC(=O)c1cc(=O)c2cc3c(=O)cc(C(=O)OC)[nH]c3c(Cl)c2[nH]1 | null | null | Cl | [Na+] | [OH-] | 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 | null | null | 1.05 g. of the diester compound prepared in Example 6 is heated at reflux for 1 hour in 20 ml. of 5% sodium hydroxide. The mixture is cooled, 10 ml. of water added, and the pH adjusted to 3 with concentrated hydrochloric acid. The bright yellow diacid is collected by filtration. It has a melting point greater than 310°... | O=C(O)c1cc(=O)c2cc3c(=O)cc(C(=O)O)[nH]c3c(Cl)c2[nH]1 | null | null | null |
238,488 | ord_dataset-960c6b9c4fc74afd90a3ebf713215626 | null | 1991-01-01T00:12:00 | true | [N:1]([CH3:4])=[C:2]=[O:3].[NH2:5][CH2:6][CH2:7][N:8]1[CH2:12][CH2:11][CH:10]([NH:13][C:14]2[N:18]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[C:17]3[CH:27]=[CH:28][CH:29]=[CH:30][C:16]=3[N:15]=2)[CH2:9]1.[Cl-].[Cl-].[Ca+2]>O1CCCC1>[F:26][C:23]1[CH:24]=[CH:25][C:20]([CH2:19][N:18]2[C:17]3[CH:27]=[CH:... | CN=C=O | NCCN1CCC(Nc2nc3ccccc3n2Cc2ccc(F)cc2)C1 | null | [Ca+2] | [Cl-] | 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 | 1.5 | A mixture of 0.9 parts of isocyanatomethane, 5.3 parts of N-[1-(2-aminoethyl)-3-pyrrolidinyl]-1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-amine and 63 parts of tetrahydrofuran was stirred for 1.5 hour at room temperature using a CaCl2 -tube. Another portion of 0.9 parts of isocyanatomethane was added and stirring was ... | CNC(=O)NCCN1CCC(Nc2nc3ccccc3n2Cc2ccc(F)cc2)C1 | null | 81 | null |
392,766 | ord_dataset-4bc8addcf9cf4845817557760d62d5b5 | null | 1998-01-01T00:02:00 | true | Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH2:12]([S-:14])[CH3:13].[Na+]>CN(C)C=O>[CH2:12]([S:14][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH3:13] | CC[S-] | Brc1cnc2ccccc2c1 | null | [Na+] | null | 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 | 3-Ethylthioquinoline is prepared starting from 2.1 g of 3-bromoquinoline and 4.2 g of sodium ethanethiolate in 30 ml of dimethylformamide analogously to Example 52d) and is purified by means of FC over 30 g of silica gel with a 1:2 mixture of diethyl ether and petroleum ether as the mobile phase. This gives the title c... | CCSc1cnc2ccccc2c1 | null | null | null |
606,311 | ord_dataset-273fda773e864aaf9b71a30a2d9f2162 | null | 2003-01-01T00:08:00 | true | O1CCCC1.[H-].[Na+].[O:8]1[C:12]2[CH:13]=[CH:14][C:15]([C:17]3[C:18]([O:36][CH2:37][CH2:38][OH:39])=[N:19][N:20]([CH3:35])[C:21]=3[NH:22][S:23]([C:26]3[CH:31]=[CH:30][C:29]([CH:32]([CH3:34])[CH3:33])=[CH:28][N:27]=3)(=[O:25])=[O:24])=[CH:16][C:11]=2[O:10][CH2:9]1.[Cl:40][C:41]1[CH:42]=[N:43][C:44](S(C)(=O)=O)=[N:45][CH:... | CS(=O)(=O)c1ncc(Cl)cn1 | CC(C)c1ccc(S(=O)(=O)Nc2c(-c3ccc4c(c3)OCO4)c(OCCO)nn2C)nc1 | null | [H-] | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)N(C)C | C1CCOC1 | null | null | null | null | null | null | null | null | null | null | 0.08 | In an oven-dried flask a solution of tetrahydrofuran (50 ml) and dimethylacetamide (3 ml) was treated with sodium hydride as a 60% dispersion in oil (460 mg) under an atmosphere of nitrogen. The reaction was stirred for 5 min and then treated with N-[4-(1,3-benzodioxol-5-yl)-3-(2-hydroxyethoxy)-1-methyl-1H-pyrazol-5-yl... | CC(C)c1ccc(S(=O)(=O)Nc2c(-c3ccc4c(c3)OCO4)c(OCCOc3ncc(Cl)cn3)nn2C)nc1 | null | 45 | null |
1,020,415 | ord_dataset-f024e9664ab64906a71a2ff6004cb3d0 | null | 2010-01-01T00:12:00 | true | Cl.Cl.[C@H]1(CN2C[CH2:18][CH:17]([NH:20][C:21]([C:23]3[NH:24][C:25]4[C:30]([CH:31]=3)=[C:29]([O:32][CH2:33][C:34]3[C:38]5[CH:39]=[C:40]([Cl:43])[CH:41]=[CH:42][C:37]=5[O:36][CH:35]=3)[CH:28]=[CH:27][CH:26]=4)=[O:22])[CH2:16][CH2:15]2)[C@@H]2N(CCCC2)CCC1.NC1C=C[C:48]([CH2:51][CH2:52][OH:53])=[CH:47]C=1>>[OH:53][CH2:52][... | Nc1ccc(CCO)cc1 | O=C(NC1CCN(C[C@@H]2CCCN3CCCC[C@H]23)CC1)c1cc2c(OCc3coc4ccc(Cl)cc34)cccc2[nH]1 | 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 | This compound is synthesized analogously to example 42 from 4-(5-Chloro-benzofuran-3-ylmethoxy)-1H-indole-2-carboxylic acid (97) and 2-(4-amino-phenyl)-ethanol. | O=C(Nc1ccc(CCO)cc1)c1cc2c(OCc3coc4ccc(Cl)cc34)cccc2[nH]1 | null | null | null |
1,762,687 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | O.Cl.[C:3]12([CH2:13][CH2:14][NH:15][C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][C:17]=3[F:25])[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2>CO.[Fe]>[C:3]12([CH2:13][CH2:14][NH:15][C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][C:17]=3[F:25])[CH2:4][CH:5]3[CH2:11][CH:9]([CH2:8][CH:7]([... | O=[N+]([O-])c1ccc(NCCC23CC4CC(CC(C4)C2)C3)c(F)c1 | null | null | [Fe] | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O | null | null | null | null | null | null | null | null | null | 25 | 0.25 | To a mixture of water (50 mL) and iron powder (0.88 g, 15.8 mmol) at 65° C. was added concentrated hydrochloric acid (1 mL) dropwise and the mixture was stirred for 15 min. The aqueous layer of the mixture was poured out, and a solution of N-(2-(adamantan-1-yl)ethyl)-2-fluoro-4-nitroaniline (0.5 g, 1.57 mmol) in MeOH (... | Nc1ccc(NCCC23CC4CC(CC(C4)C2)C3)c(F)c1 | null | 84.4 | null |
1,762,750 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [F:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Br[C:10]([CH3:17])([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12].C([O-])([O-])=O.[K+].[K+].O>CC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][C:10]([CH3:17])([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12] | CCOC(=O)C(C)(C)Br | Oc1cccc(F)c1 | null | O=C([O-])[O-] | [K+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CC(C)=O | null | null | null | null | null | null | null | null | null | 25 | null | A mixture of 3-fluorophenol (3.36 g, 30.0 mmol), ethyl 2-bromo-2-methylpropanoate (8.78 g, 45.0 mmol) and K2CO3 (6.22 g, 45.0 mmol) in acetone (50 mL) was refluxed overnight. The mixture was cooled to rt and 60 mL of water was added. The resulting mixture was extracted with DCM (40 mL×2). The combined organic phases we... | CCOC(=O)C(C)(C)Oc1cccc(F)c1 | null | 47.1 | null |
1,051,950 | ord_dataset-373415d3e0e54004837cf4831e67666f | null | 2011-01-01T00:05:00 | true | [CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[C:11]([N+:14]([O-])=O)[CH:12]=[CH:13][C:7]=2[CH:6]=1)=[O:4]>CN(C=O)C.[Pd]>[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[C:11]([NH2:14])[CH:12]=[CH:13][C:7]=2[CH:6]=1)=[O:4] | COC(=O)c1cc2ccc([N+](=O)[O-])cc2s1 | null | null | [Pd] | null | 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 | 25 | 96 | To a stirring solution of 6-nitro -benzo[b]thiophene-2-carboxylic acid methyl ester (3.9 g, 15.8 mmol) in DMF (120 mL) was added 10% Pd/C (700 mg, 10 %). The reaction was charged with H2, degassed and refilled with hydrogen three times. The slurry was stirred at RT for 4 days at balloon pressure, then filtered through ... | COC(=O)c1cc2ccc(N)cc2s1 | null | null | null |
557,263 | ord_dataset-f483e698250b4da0a84f425c7bfa965a | null | 2002-01-01T00:08:00 | true | [CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C@:14](CC2C=CC=CC=2)(O)[C@@H:13](O)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1 | O=C(OCc1ccccc1)N1CC[C@@](O)(Cc2ccccc2)[C@@H](O)C1 | null | null | CN(C)c1ccncc1 | O=C([O-])O | [Na+] | 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 | 16 | To a solution of 43.0 g (126 mmol) (3R,4R) and (3S,4S)-4-benzyl-3,4-dihydroxy-piperidine-1-carboxylic acid benzyl ester and 23.1 g (189 mmol) DMAP in 600 ml CH2Cl2 were added dropwise under argon 500 ml (340 mmol, 0.70 N) (S)-N-trifluoroacetyl-prolinechloride. The reaction mixture was stirred for 16 hours at r.t. and t... | O=C(OCc1ccccc1)N1CCCCC1 | null | null | null |
1,337,949 | ord_dataset-08852243bba44cb28769a5833f1515fe | null | 2013-01-01T00:09:00 | true | [OH:1][C:2]1[CH:3]=[C:4]([C:10](=O)[CH3:11])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].Cl.[F:14][C:15]1[CH:23]=[CH:22][C:18]([CH2:19][O:20][NH2:21])=[CH:17][CH:16]=1>>[F:14][C:15]1[CH:23]=[CH:22][C:18]([CH2:19][O:20]/[N:21]=[C:10](/[C:4]2[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([OH:1])[CH:3]=2)\[CH3:11])=[CH:17][CH:16]=1 | NOCc1ccc(F)cc1 | COc1ccc(C(C)=O)cc1O | 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 | Acetophenone 12 (50 mg, 0.301 mmol) was condensed with O-(4-fluorobenzyl)hydroxylamine hydrochloride (29) (58 mg, 0.327 mmol) according to the general procedure II-B defined above. After being heated for 24 h the reaction mixture was cooled and the solvent removed under reduced pressure. The ensuing residue was dissolv... | COc1ccc(/C(C)=N/OCc2ccc(F)cc2)cc1O | null | 80.4 | null |
631,657 | ord_dataset-0a66204fc43e49c2922e6f9107e6b62f | null | 2004-01-01T00:03:00 | true | [NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)=[CH:9][N:8]([CH:24]3[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]3)[C:4]=2[N:5]=[CH:6][N:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[O:17]([C:14]1[CH:13]=[CH:12][C:11]([C:10]2[C:3]3[C:2]([NH2:1])=[... | CC(C)(C)OC(=O)N1CCC(n2cc(-c3ccc(Oc4ccccc4)cc3)c3c(N)ncnc32)CC1 | 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 | ClCCl | null | null | null | null | null | null | null | null | null | 25 | 20 | To a solution of tert-butyl 4-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-1-piperidinecarboxylate (0.69 g, 1.4 mmol) in dry CH2Cl2 (25 ml) at 0° C. was added TFA (5 ml). The solution was stirred at room temperature for 20 hr and the solvent evaporated. NaOH solution (5N, 10 ml) was added and the resul... | Nc1ncnc2c1c(-c1ccc(Oc3ccccc3)cc1)cn2C1CCNCC1 | null | 92.7 | null |
345,998 | ord_dataset-d0003732f14e4648a00d341275654590 | null | 1996-01-01T00:11:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[C:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH:16]=1.[O:17]1[CH2:19][C@H:18]1[CH2:20][O:21][C:22]1[CH:30]=[CH:29][CH:28]=[C:27]2[C:23]=1[CH:24]=[CH:25][NH:26]2>CO.CS(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[C:11]1[CH2:12][CH2:13][... | Clc1cccc2c(C3=CCNCC3)c[nH]c12 | c1cc(OC[C@@H]2CO2)c2cc[nH]c2c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CS(C)=O | CO | null | null | null | null | null | null | null | null | null | null | null | The title compound was prepared in a fashion similar to that described in Example 193 from 7-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (0.50 g, 2.2 mmol) and (S)-(+)-4-(oxiranylmethoxy)-1H-indole (0.41 g, 2.2 mmol). The product was isolated as a white foam. Yield 370 mg (41%). mp 85°-90° C. FDMS m/e=421 (M+ o... | O[C@H](COc1cccc2[nH]ccc12)CN1CC=C(c2c[nH]c3c(Cl)cccc23)CC1 | null | null | null |
1,285,840 | ord_dataset-d5c54236ecd94d61aaa071461bcfc426 | null | 2013-01-01T00:04:00 | true | [Se](O)(O)=[O:2].[CH3:5][O:6][C:7](=[O:21])[CH2:8][C:9]1[C:18]([Cl:19])=[CH:17][CH:16]=[C:15]2[C:10]=1[N:11]=[C:12]([CH3:20])[CH:13]=[N:14]2>O1CCOCC1.O>[CH3:5][O:6][C:7](=[O:21])[CH2:8][C:9]1[C:18]([Cl:19])=[CH:17][CH:16]=[C:15]2[C:10]=1[N:11]=[C:12]([CH:20]=[O:2])[CH:13]=[N:14]2 | O=[Se](O)O | COC(=O)Cc1c(Cl)ccc2ncc(C)nc12 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | O | null | null | null | null | null | null | null | null | null | 100 | 1 | Selenious acid (645 mg, 5.00 mmol, 1.1 equiv) was added to a solution of (6-chloro-3-methyl-quinoxalin-5-yl)-acetic acid methyl ester in dioxane (30 ml). The reaction mixture was heated to 100° C. After 60 minutes, an additional portion of selenious acid (645 mg) was added, and heating was continued for another 60 minu... | COC(=O)Cc1c(Cl)ccc2ncc(C=O)nc12 | null | 81 | null |
304,154 | ord_dataset-180e296d6d6245638d4d22a59120ea01 | null | 1995-01-01T00:02:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[CH2:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1>C(O)(=O)C.[Pt]=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[CH2:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1 | COc1cccc(Cc2ccncc2)c1 | null | null | O=[Pt] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | 2 | A mixture of 4-(3-methoxybenzyl)pyridine (25 g, 126 mmole) and platinum oxide (2.4 g) in acetic acid (250 ml) was hydrogenated for 2 hr. The catalyst was removed and the solution concentrated in vacuo. The residue was dissolved in water and the solution basified with sodium hydroxide. The basic mixture was extracted wi... | COc1cccc(CC2CCNCC2)c1 | null | 87.4 | null |
80,139 | ord_dataset-2d589ad46f82417ab9ddc07f7655411c | null | 1981-01-01T00:04:00 | true | [OH:1][C:2]([CH3:20])([C:9]([CH3:19])=[CH:10][CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:3][C:4]([O:6]CC)=[O:5].[OH-].[Na+].[Br:23]Br>CO.C(=O)([O-])O.[Na+].O.CO>[OH:1][C:2]1([CH3:20])[C:9]([CH3:19])([Br:23])[CH:10]([CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:6][C:4](=[O:5])[C... | BrBr | CCOC(=O)CC(C)(O)C(C)=CC=Cc1ccccc1 | null | O=C([O-])O | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O | null | null | null | null | null | null | null | null | null | null | 0.5 | The carboxylic acid (1.09 g) prepared by hydrolyzing 12.20 g of ethyl 3-hydroxy-3,4-dimethyl-7-phenyl-4,6-heptadienoate with 4 N sodium hydroxide solution in 60 ml of methanol, was dissolved in a solution of 700 mg of sodium hydrogen carbonate in 40 ml of a solvent mixture of water-methanol (1:1) and a solution of 1.06... | CC1(O)CC(=O)OC(C=Cc2ccccc2)C1(C)Br | null | 34.8 | null |
132,841 | ord_dataset-34cf5f1378de4e34844aea93a2f9a9d3 | null | 1985-01-01T00:08:00 | true | [OH:1][C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5](=[O:13])(=[O:12])[N:4]([CH3:14])[C:3]=1[C:15](Cl)=[O:16].[NH2:18][C:19]1[CH:24]=[N:23][CH:22]=[C:21]([Cl:25])[N:20]=1.O>CN(C)C=O>[Cl:25][C:21]1[N:20]=[C:19]([NH:18][C:15]([C:3]2[N:4]([CH3:14])[S:5](=[O:13])(=[O:12])[C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[C:2]... | Nc1cncc(Cl)n1 | CN1C(C(=O)Cl)=C(O)c2ccccc2S1(=O)=O | 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 | 24 | 1.23 g (4.5 mmols) of 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylic acid chloride-1,1-dioxide were dissolved in 10 ml of dimethylformamide, and 1.3 g (10 mmols) of 2-amino-6-chloro-pyrazine were added in portions thereto. The reaction mixture was stirred for 24 hours at room temperature and was then mixed with 4... | CN1C(C(=O)Nc2cncc(Cl)n2)=C(O)c2ccccc2S1(=O)=O | null | 24.2 | null |
69,918 | ord_dataset-06d4002fc4d34860a0688cba690e12dc | null | 1980-01-01T00:09:00 | true | [CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:12][CH2:13][NH2:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:26][C:27]1[CH:37]=[CH:36][C:30]([NH:31][CH2:32][C:33](O)=[O:34])=[CH:29][CH:28]=1>C1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2... | O=C(O)CNc1ccc(Cl)cc1 | NCCc1ccc(OCc2ccccc2)c(OCc2ccccc2)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccccc1 | null | null | null | null | null | null | null | null | null | null | 190 | 3 | A mixture of 3,4-dibenzyloxyphenethylamine (36.2 g) and p-chloroanilinoacetic acid (20 g) was stirred for 3 hours at 190° C. The reaction mixture was dissolved in benzene. The solution was washed with a diluted potassium carbonate aqueous solution and dried. The solvent was distilled off from the benzene solution and t... | O=C(CNc1ccc(Cl)cc1)NCCc1ccc(OCc2ccccc2)c(OCc2ccccc2)c1 | null | 50.4 | null |
1,351,845 | ord_dataset-6034127657614f02860ed057b62b882e | null | 2013-01-01T00:10:00 | true | [F:1][C:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[C:5]([F:17])=[CH:4][C:3]=1[C:18]1[N:22]([C@H:23]2[CH2:27][CH2:26][O:25][CH2:24]2)[N:21]=[CH:20][C:19]=1[C:28]([O:30][CH2:31][CH3:32])=[O:29].I[C:34]1[C:39]([CH3:40])=[CH:38][N:37]=[C:36]([O:41][CH3:42])[C:35]=1[CH3:43].C(=O)([O-])[O-].[Cs+].[Cs+].O1CCOCC1>C1C=CC([P]([Pd]([P]... | COc1ncc(C)c(I)c1C | CCOC(=O)c1cnn([C@H]2CCOC2)c1-c1cc(F)c(B2OC(C)(C)C(C)(C)O2)cc1F | null | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | O | null | null | null | null | null | null | null | null | null | 25 | null | Ethyl 5-(4-bromo-2,5-difluorophenyl)-1-((S)-tetrahydrofuran-3-yl)-1H-pyrazole-4-carboxylate obtained in Preparation Example 11-1 (4.31 g), bis(pinacolato)diboron (3.27 g), potassium acetate (3.16 g) and Pd(dppf)Cl2-DCM complex (439 mg) were added to DMF (41.6 mL), and the mixture was stirred at 95° C. in a nitrogen atm... | CCOC(=O)c1cnn([C@H]2CCOC2)c1-c1cc(F)c(-c2c(C)cnc(OC)c2C)cc1F | null | null | null |
592,617 | ord_dataset-7a74d48eeefd45aba53e7258f3ae067a | null | 2003-01-01T00:04:00 | true | C(OC(=O)[N:7](C)[C@@H:8]([C:16](=[O:24])[NH:17][CH2:18][CH:19]1[CH2:23][CH2:22][CH2:21][O:20]1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(C)(C)C.F[C:28](F)(F)C(O)=O.C(=O)([O-])O.[Na+].C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH3:28][C@@:8]([NH2:7])([CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14]... | O=C(O)C(F)(F)F | CN(C(=O)OC(C)(C)C)[C@H](Cc1ccccc1)C(=O)NCC1CCCO1 | null | O=C([O-])O | O=C([O-])[O-] | [Na+] | 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 | 1 | Methyl-((1R)-2-phenyl-1-((tetrahydrofuran-2-ylmethyl)carbamoyl)ethyl)carbamic acid tert-butyl ester (5.5 g; 15.2 mmol) was dissolved in methylene chloride (20 mL) and trifluoroacetic acid (20 mL) was added. The reaction mixture was stirred for 1 hour at room temperature. Methylene chloride (100 mL) and an aqueous solut... | C[C@@](N)(Cc1ccccc1)C(=O)NCC1CCCO1 | null | null | null |
949,584 | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | null | 2010-01-01T00:04:00 | true | CCO.C1(C)C(S([N:13]2[CH:17]=[CH:16][CH:15]=[C:14]2[C:18](=[O:32])[C:19]2[CH:24]=[CH:23][C:22]([NH:25]C(=O)C(F)(F)F)=[CH:21][CH:20]=2)(=O)=O)=CC=CC=1.[OH-].[K+]>CCOC(C)=O>[NH2:25][C:22]1[CH:23]=[CH:24][C:19]([C:18]([C:14]2[NH:13][CH:17]=[CH:16][CH:15]=2)=[O:32])=[CH:20][CH:21]=1 | Cc1ccccc1S(=O)(=O)n1cccc1C(=O)c1ccc(NC(=O)C(F)(F)F)cc1 | null | null | [K+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | CCOC(C)=O | null | null | null | null | null | null | null | null | null | 25 | null | To a stirred EtOH (4 mL) solution containing N-toluenesulfonyl-2-(4-(trifluoroacetylamino)benzoyl)pyrrole (0.500 g, 1.15 mmol), was added 40% KOH solution (2 mL) and the mixture was heated at reflux until thin layer chromatography (TLC) analysis showed complete conversion of the starting material. The resulting solutio... | Nc1ccc(C(=O)c2ccc[nH]2)cc1 | null | 91.5 | null |
190,108 | ord_dataset-be83cbc722064f3696975001242f9f1a | null | 1989-01-01T00:05:00 | true | [C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])[CH:8]=O)([CH3:4])([CH3:3])[CH3:2].[Br-].[CH3:19][N:20]1[CH2:24][CH2:23][CH:22]([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:21]1=[O:44].C(N(CC)CC)C>C(O)C>[CH3:19][N:20]1[CH2:24][CH2:23][C:22](=[CH:8][C:7]2[CH:6]=[C:5]([C:1]([CH3... | CC(C)(C)c1cc(C=O)cc(C(C)(C)C)c1O | CN1CCC([P+](c2ccccc2)(c2ccccc2)c2ccccc2)C1=O | null | [Br-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | CCN(CC)CC | null | null | null | null | null | null | null | null | null | null | null | 1.2 g of 3,5-di-tert-butyl-4-hydroxybenzaldehyde, 2.5 g of (N-methyl-2-pyrrolidone-3-yl)triphenylphosphonium bromide and 1.0 ml of triethylamine were heated under reflux in ethanol for two hours. After distilling the ethanol off, the residue was dissolved in chloroform, washed with water followed by a saturated saline ... | CN1CCC(=Cc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)C1=O | null | 61.9 | null |
317,934 | ord_dataset-eb32c2b9cbdf4fc39ce6c9fe0fa11430 | null | 1995-01-01T00:10:00 | true | [C@@H:1]12[O:9][CH2:8][C@@H:6]([O:7]1)[CH:5]=[CH:4][C@@H:2]2[OH:3].[S:10](Cl)([CH3:13])(=[O:12])=[O:11].Cl>N1C=CC=CC=1>[S:10]([O:3][C@H:2]1[CH:4]=[CH:5][C@H:6]2[CH2:8][O:9][C@@H:1]1[O:7]2)([CH3:13])(=[O:12])=[O:11] | CS(=O)(=O)Cl | O[C@H]1C=C[C@H]2CO[C@@H]1O2 | null | Cl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | 0.25 g (1.98 mmol) of 1,6-anhydro-3,4-dideoxy-β-D-threo-hex-3-enopyranose were dissolved in 2 ml of pyridine, and 0.34 g (3.00 mmol) of mesyl chloride were dropped in this mixture under ice-water cooled conditions. The resultant solution was stirred at 0° C. for 3.5 hours and then stored in a refrigerator overnight. Th... | CS(=O)(=O)O[C@H]1C=C[C@H]2CO[C@@H]1O2 | null | 63.7 | null |
949,947 | ord_dataset-3feb2a95f66e4706a4a50c977ccd9bf8 | null | 2010-01-01T00:04:00 | true | [H-].[Na+].[CH3:3][C:4]12[C:15](=[O:16])[NH:14][C:12]3[C:13]1=[C:8]([CH:9]=[CH:10][CH:11]=3)[NH:7][C:6](=[O:17])[CH2:5]2.Br[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>CN(C=O)C>[CH3:3][C:4]12[C:15](=[O:16])[N:14]([CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:12]3[C:13]1=[C:8]([CH... | CC12CC(=O)Nc3cccc(c31)NC2=O | CC(C)(C)OC(=O)CBr | null | [H-] | [Na+] | 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 | 25 | 1 | Sodium hydride (71 mg of a 60% dispersion in mineral oil, 1.78 mmol) was added to a solution of (±)-2a-methyl-2a,5-dihydropyrrolo[4,3,2-de]quinoline-2,4(1H,3H)-dione from Step C (298 mg, 1.47 mmol) in DMF (3 mL) at 0° C. After 1 h, tert-butyl bromoacetate (0.219 mL, 1.48 mmol) was added dropwise and the reaction mixtur... | CC(C)(C)OC(=O)CN1C(=O)C2(C)CC(=O)Nc3cccc1c32 | null | null | null |
1,293,406 | ord_dataset-de51ecc8d4434bacaa8bc32d7d73484c | null | 2013-01-01T00:05:00 | true | [CH2:1]([C@:4]1([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:12])[CH2:6][CH2:5]1)[CH:2]=C.FC1C=CC(C2(CCO)[O:36]C(=O)NCC2)=CC=1>>[CH3:14][C:13]([CH3:15])([CH3:16])[C@@H:11]([N:7]1[CH2:6][CH2:5][C:4]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[C... | O=C1NCCC(CCO)(c2ccc(F)cc2)O1 | C=CC[C@@]1(c2ccc(F)cc2)CCN([C@@H](C)C(C)(C)C)C(=O)O1 | 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 | (S)-6-allyl-3-((2S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one [Isomer 2] (500 mg, 1.57 mmol) was converted to (R)-3-(S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-6-(2-hydroxyethyl)-1,3-oxazinan-2-one [Isomer 2] (300 mg, 59%) following a procedure analogous to that described immediately above. LC-MS... | C[C@H](N1CCC(CCO)(c2ccc(F)cc2)OC1=O)C(C)(C)C | null | null | null |
447,492 | ord_dataset-a4f0b79f6b9847168861270b79f84afa | null | 1999-01-01T00:11:00 | true | [C:1]([C:3]1[C:4]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH3:22])=[CH:16][CH:15]=2)=[N:5][NH:6][C:7]=1[N:8]=[CH:9][N:10](C)C)#[N:2].Cl.[Cl:24][C:25]1[CH:26]=[C:27]([CH:29]=[CH:30][CH:31]=1)N>CO>[Cl:24][C:25]1[CH:31]=[C:30]([NH:2][C:1]2[N:10]=[CH:9][N:8]=[C:7]3[NH:6][N:5]=[C:4]([NH:13][C:14]4[CH:15]=[CH:16][... | Nc1cccc(Cl)c1 | CCOc1ccc(Nc2n[nH]c(N=CN(C)C)c2C#N)cc1 | null | Cl | 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 | 10 | null | A mixture of 5.8 g (19.44 mmol) of 4-cyano-5-(dimethylamino-methyleneamino)-3-(4-ethoxy-phenylamino)-pyrazole, 3.51 g (21.4 mmol) of 3-chloro-aniline hydrochloride and 40 ml of methanol is heated under reflux for 15 hours. Cooling to 10° C., filtering and washing the filter residue with methanol and diethyl ether yield... | CCOc1ccc(Nc2n[nH]c3ncnc(Nc4cccc(Cl)c4)c23)cc1 | null | null | null |
1,450,447 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:12]=[N:13][C:14]([CH:18]2[CH2:20][CH2:19]2)=[C:15]([Cl:17])[CH:16]=1)[C:5]#[N:6].[CH3:21][O:22][C:23]1[C:28](B(O)O)=[CH:27][CH:26]=[CH:25][N:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O>[Cl:17][C:15]1[CH:16]=[C:11]([O:10][C:9]2[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH... | COc1ncccc1B(O)O | N#Cc1ccc(Oc2cnc(C3CC3)c(Cl)c2)c(Br)c1 | null | O=C([O-])[O-] | [Cs+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | C1COCCO1 | null | null | null | null | null | null | null | null | null | 75 | null | 3-bromo-4-(5-chloro-6-cyclopropylpyridin-3-yloxy)benzonitrile (Preparation 38, 485 mg, 1.37 mmol), 2-methoxypyridin-3-ylboronic acid (233 mg, 1.53 mmol) and cesium carbonate were suspended in dioxane (6 mL) and water (3 mL). The suspension was degassed 20 minutes with nitrogen then tetrakis-triphenylphosphinepalladium ... | COc1ncccc1-c1cc(C#N)ccc1Oc1cnc(C2CC2)c(Cl)c1 | null | 92.3 | null |
1,128,390 | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | null | 2012-01-01T00:01:00 | true | [CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[C:18]([C:22](=[CH2:27])[C:23]([F:26])([F:25])[F:24])=[N:17][N:16]=[CH:15]2>CO.[Pd]>[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:... | C=C(c1nncc2cc(-c3cc(C(=O)OC)ccc3C)ccc12)C(F)(F)F | 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 | null | A solution of methyl 4-methyl-3-(1-(1,1,1-trifluoroprop-2-en-2-yl)phthalazin-6-yl)benzoate (200 mg, 537 μmol) in methanol (3000 μl) was added palladium (10 wt. % on activated carbon; 22.9 mg, 215 μmol) and hydrogenated (double-walled balloon pressure) at room temperature for 20 h, during which LC-MS indicated complete ... | COC(=O)c1ccc(C)c(-c2ccc3c(C(C)C(F)(F)F)nncc3c2)c1 | null | 45.3 | null |
901,716 | ord_dataset-de6bce51790e4004a27e1a8f2bcc7ded | null | 2009-01-01T00:08:00 | true | [CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][NH2:21])[CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7]>N1C=CC=CC=1>[C:6]([O:10][C:11]([N:13]1[CH2:14][CH2:15][N:16]([CH2:19][CH2:20][NH:21][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:17][CH2:18]1)=[O:12])([CH3:9])([CH3:8])[CH3:7... | CS(=O)(=O)Cl | CC(C)(C)OC(=O)N1CCN(CCN)CC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | 12 | Methanesulfonyl chloride (0.7 mL, 9.0 mmol) was added to a cooled solution of 4-(2-amino-ethyl)-piperazine-1-carboxylic acid tert-butyl ester (1.33 g, 5.8 mmol) in pyridine (25.0 mL). The reaction was stirred for 12 h and partitioned between partitioned between aqueous sodium bicarbonate and methylene chloride. The org... | CC(C)(C)OC(=O)N1CCN(CCNS(C)(=O)=O)CC1 | null | 39.3 | null |
132,836 | ord_dataset-34cf5f1378de4e34844aea93a2f9a9d3 | null | 1985-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10](=[O:12])(=[O:11])[N:9]([CH3:13])[C:8]([C:14]([O:16]C)=O)=[C:7]([OH:18])[C:6]=2[CH:19]=1.[NH2:20][C:21]1[CH:26]=[N:25][CH:24]=[C:23]([Cl:27])[N:22]=1>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10](=[O:11])(=[O:12])[N:9]([CH3:13])[C:8]([C:14]([NH:20][C:21]3[CH:26]=[N:25][CH:... | Nc1cncc(Cl)n1 | COC(=O)C1=C(O)c2cc(Cl)ccc2S(=O)(=O)N1C | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | Cc1ccccc1C | null | null | null | null | null | null | null | null | null | null | null | null | 3.04 (10 mmols) of methyl 6-chloro-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide and 1.5 g (12 mmols) of 2-amino-6-chloro-pyrazine were reacted in 150 ml of xylene analogous to Example 2. 3.2 g (80% of theory) of 6-chloro-N-(6-chloro-pyrazin-2-yl)-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamid... | CN1C(C(=O)Nc2cncc(Cl)n2)=C(O)c2cc(Cl)ccc2S1(=O)=O | null | 80 | null |
633,613 | ord_dataset-de283386b8034acd99fba96d3c7d3227 | null | 2004-01-01T00:04:00 | true | S(Cl)([Cl:3])=O.[O:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]2[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[CH:17][CH:16]=2)=[CH:7][CH2:6]1>ClCCl>[O:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]2[CH:23]=[CH:22][C:18]([C:19]([Cl:3])=[O:20])=[CH:17][CH:16]=2)=[CH:7][CH2:6]1 | O=S(Cl)Cl | O=C(O)c1ccc(C2=CCOc3ccccc32)cc1 | 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 | 4 | Thionyl chloride (2 mL) was added to a suspension of 4-(2H-chromen-4-yl)benzoic acid from reaction 34c (0.415 g, 1.6 mmol) in dichloromethane (10 mL) at room temperature. The reaction was stirred for 4 h, concentrated in vacuo to give 4-(2H-chromen-4-yl)benzoyl chloride (0.445 g, 99%) as a yellow solid. | O=C(Cl)c1ccc(C2=CCOc3ccccc32)cc1 | null | 99 | null |
1,036,262 | ord_dataset-3af92aec23dc4810b92eb0d8c60023ee | null | 2011-01-01T00:03:00 | true | [CH3:1][C:2]([CH3:32])([CH3:31])[C:3](=[O:30])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:17]2[S:21][C:20]3[CH:22]=[CH:23][C:24]([C:26]([OH:28])=[O:27])=[CH:25][C:19]=3[CH:18]=2)([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:8][C:7]=1[CH3:29].[BH4-].[Na+]>>[CH2:13]([C:12]([C:17]1[S:21][C:20]2[CH:22]=[CH:23][C:24]([C:26](... | CCC(CC)(c1ccc(OCC(=O)C(C)(C)C)c(C)c1)c1cc2cc(C(=O)O)ccc2s1 | null | null | [BH4-] | [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 | null | null | 2-{1-[4-(3,3-Dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-benzo[b]thiophene-5-carboxylic acid (330 mg, 0.730 mmol) is reduced using NaBH4 (55 mg, 1.46 mmol) in a reaction analogous to Example 2 to afford the title compound (0.306 g, 92%). | CCC(CC)(c1ccc(OCC(O)C(C)(C)C)c(C)c1)c1cc2cc(C(=O)O)ccc2s1 | null | 92.2 | null |
7,287 | ord_dataset-653be8036d754ce7b8a1c4cd419eaf55 | null | 1976-01-01T00:05:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[S:10][C:9]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20]Cl)=[CH:14][CH:13]=3)=[N:8][C:7]=2[CH:22]=1.[NH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1>COCCO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[S:10][C:9]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][N:23]4[CH2:27... | COc1ccc2sc(Nc3ccc(OCCCl)cc3)nc2c1 | C1CCNC1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | COCCO | null | null | null | null | null | null | null | null | null | null | null | null | A mixture of 5-methoxy-2-[4-(2-chloroethoxy)anilino]benzothiazole (200 g.), pyrrolidine (144 ml.) and 2-methoxyethanol (1 liter) is boiled under reflux for 16 hours. The mixture is evaporated from the steam bath at reduced pressure and the residue dissolved in approximately 2N hydrochloric acid. The solution is washed ... | COc1ccc2sc(Nc3ccc(OCCN4CCCC4)cc3)nc2c1 | null | null | null |
1,060,317 | ord_dataset-ffbef48837674f39816de887b5dc8bae | null | 2011-01-01T00:06:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:26])[CH:6]=[CH:7][C:8]=1[C:9]1[O:10][C:11]([C:14]2[C:15]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:16][O:17][C:18]=2[CH3:19])=[N:12][N:13]=1.C(N(CC)C(C)C)(C)C.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>C1COCC1.CN(C)C1C=CN=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:26]([S:37]([CH3:36])(=... | COc1cc(N)ccc1-c1nnc(-c2c(-c3ccccc3)noc2C)o1 | CS(=O)(=O)Cl | null | CN(C)c1ccncc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | CCN(C(C)C)C(C)C | null | null | null | null | null | null | null | null | null | 25 | 18 | To a solution of 3-methoxy-4-[5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazol-2-yl]-phenylamine (200 mg, 0.57 mmol) in THF (2 mL) were added N,N-diisopropyl ethyl amine (0.15 mL, 0.86 mmol), 4-dimethylaminopyridine (8 mg, 0.06 mmol) and methanesulfonyl chloride (53 μL, 0.69 mmol). The resulting suspension was then... | COc1cc(N(S(C)(=O)=O)S(C)(=O)=O)ccc1-c1nnc(-c2c(-c3ccccc3)noc2C)o1 | null | 117.8 | null |
463,585 | ord_dataset-6c36eb0f817d4144988b8963c5d58879 | null | 2000-01-01T00:05:00 | true | CC(=C[N:5]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:6]1[CH:11]=CC=C[CH:7]=1)C.[C:19]1([CH3:26])[CH:24]=[CH:23][CH:22]=[C:21](C)[CH:20]=1>ClCCl.[Cl-].[Zn+2].[Cl-]>[CH3:7][C:6]1([CH3:11])[CH2:26][C:19]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:5]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18... | CCCCCCCN(C=C(C)C)c1ccccc1 | Cc1cccc(C)c1 | 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 | N-(2-methylprop-2-en-3-yl)N-n-heptyl aniline (0.38 mole), zinc chloride (0.4 mole) and m-xylene (200 cm3) were refluxed for 17 hours before cooling and dissolving in dichloromethane. The dichloromethane was filtered and washed with water, separated, dried over magnesium sulphate, filtered and evaporated to leave an oil... | CCCCCCCN1c2ccccc2CC1(C)C | null | 95.8 | null |
861,455 | ord_dataset-93908aaae836460ebd48d733eccad483 | null | 2009-01-01T00:01:00 | true | [C:1]([C:3]1[CH:8]=[CH:7][C:6](=[O:9])[N:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:4]=1[S-:16])#[N:2].[Na+].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].O>CCO>[CH2:23]([O:22][C:20]([C:19]1[S:16][C:4]2[N:5]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:6](=[O:9])[CH:7]=[CH:8][C:3]=2[C:1]=1[NH2:2])=[O:2... | N#Cc1ccc(=O)n(-c2ccccc2)c1[S-] | CCOC(=O)CBr | null | [Na+] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | O | CCO | null | null | null | null | null | null | null | null | null | null | null | A mixture of Example 1 (0.34 g at 100%) and ethyl bromoacetate (0.197 mL) in EtOH (6 mL) was stirred at room temperature for 1 h. H2O (10 mL) was then added. The solid was filtered and washed with more H2O (2 mL). The product was dried under vacuum at 40° C. to constant weight to give the title compound as a pale pink ... | CCOC(=O)c1sc2c(ccc(=O)n2-c2ccccc2)c1N | null | null | null |
1,450,674 | ord_dataset-a86112d52cd54525a5e36d41f18aced2 | null | 2014-01-01T00:07:00 | true | [NH2:1][C:2]1=[N:3][C:4](=[O:30])[N:5]([CH3:29])/[C:6]/1=[CH:7]\[CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:16]=2[C:25]([F:28])([F:27])[F:26])[CH2:10][CH2:9]1.[CH2:31](N)[C:32]#[CH:33]>C1(C)C=CC=CC=1>[F:27][C:25]([F:26])([F:28])[C:16]1[CH:17]=[C:18]([C:21](... | C#CCN | CN1C(=O)N=C(N)/C1=C/C1CCN(Cc2ccc(C(F)(F)F)cc2C(F)(F)F)CC1 | null | null | 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 | 100 | 8 | To a solution of (5Z)-4-amino-5-({1-[2,4-bis(trifluoromethyl)benzyl]piperidin-4-yl}methylidene)-1-methyl-1,5-dihydro-2H-imidazol-2-one (1.50 g) in toluene (10 mL) was added propargylamine (1.90 g) at room temperature. The reaction mixture was stirred at 100° C. overnight. The residue was purified by silica gel column c... | C#CCNC1=NC(=O)N(C)/C1=C\C1CCN(Cc2ccc(C(F)(F)F)cc2C(F)(F)F)CC1 | null | 53.3 | null |
309,088 | ord_dataset-081613ef79bd4110aacc146b4465f086 | null | 1995-01-01T00:05:00 | true | Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][O:10][CH2:11][CH:12]([O:31][CH3:32])[CH2:13][O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:4]=1.[NH:33]1[CH:37]=[CH:36][N:35]=[CH:34]1>C1(C)C=CC=CC=1>[CH2:15]([O:14][CH2:13][CH:12... | CCCCCCCCCCCCCCCCOCC(COCc1cccc(CBr)c1)OC | c1c[nH]cn1 | null | null | 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 | 80 | null | a mixture of 2.4 g of 1-(bromomethyl)-3-[[3-(hexadecyloxy)-2-methoxypropoxy]methyl]benzene, 2.54 g of imidazole and 30 ml of toluene was heated at 80° C. under argon in a pressure bottle for 4 hours and then evaporated. The residue was purified by chromatography, giving 2.02 g of the desired product as a colorless oil. | CCCCCCCCCCCCCCCCOCC(COCc1cccc(Cn2ccnc2)c1)OC | null | 86.3 | null |
946,248 | ord_dataset-ed680843f6d14f5c9901869b2a06b4a4 | null | 2010-01-01T00:03:00 | true | [C:1](Cl)(=[O:3])[CH3:2].[C:5]([Si:9]([CH3:35])([CH3:34])[O:10][CH2:11][C:12]([C:26]1[CH:31]=[CH:30][C:29]([F:32])=[C:28]([F:33])[CH:27]=1)=[C:13]([C:16]1[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=1)[CH2:14][OH:15])([CH3:8])([CH3:7])[CH3:6].CCN(CC)CC>C(Cl)Cl>[C:5]([Si:9]([CH3:35])([CH3:34])[... | CC(C)(C)[Si](C)(C)OCC(=C(CO)c1ccc(S(C)(=O)=O)cc1)c1ccc(F)c(F)c1 | CC(=O)Cl | null | null | 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 | null | 12 | Diisobutylaluminum hydride (1.0 M solution in dichloromethane) was added dropwise to a solution of 3-(3,4-Difluoro-phenyl)-4-(4-methanesulfonyl-phenyl)-H-furan-2-one (15.0 g, 42.8 mmol) and CH2Cl2 at 0° C. Upon completion of the addition, the solution was allowed to warm to rt, and maintained for 12 h. The reaction mix... | CC(=O)OCC(=C(CO[Si](C)(C)C(C)(C)C)c1ccc(F)c(F)c1)c1ccc(S(C)(=O)=O)cc1 | null | null | null |
1,540,350 | ord_dataset-cac8df8aff894288876df4e093c9877f | null | 2015-01-01T00:02:00 | true | [OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8](=[O:19])[CH2:9][O:10][C:11]2[C:12](=[O:18])[N:13]([CH3:17])[N:14]=[CH:15][CH:16]=2)[CH2:4][CH2:3]1.[Cl:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1O>>[Cl:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[O:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8](=[O:19])[CH2:9][O:10][C... | Oc1ccc(F)cc1Cl | Cn1nccc(OCC(=O)N2CCC(O)CC2)c1=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 | Compound 22 is prepared from intermediate 5c and from 2-chloro-4-fluoro-phenol following synthesis method 3 (yield: 18%). | Cn1nccc(OCC(=O)N2CCC(Oc3ccc(F)cc3Cl)CC2)c1=O | null | 18 | null |
1,507,759 | ord_dataset-1a1aa5d1c3224edca0aec6e3398da985 | null | 2014-01-01T00:11:00 | true | Br[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1>CC#N>[CH2:8]([O:7][C:5](=[O:6])[CH2:4][CH2:3][CH2:2][N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)[CH3:9] | C1COCCN1 | CCOC(=O)CCCBr | null | null | null | 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 | 80 | null | A solution of ethyl 4-bromobutyrate (681 mg) in MeCN (5.0 mL) was treated with morpholine (0.61 mL) at rt. The reaction mixture was heated to 80° C. for 3 h and cooled down to rt. It was concentrated under reduced pressure, diluted with EA and the org. layer was washed with water and brine, dried over MgSO4, filtered a... | CCOC(=O)CCCN1CCOCC1 | null | 96 | null |
1,246,255 | ord_dataset-c544c0c663f54dbea4ddb52ddde7934e | null | 2013-01-01T00:01:00 | true | [C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=2[C:24]#[N:25])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>N.CCO.[Ni]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:21])([F:22])[F:23])=[CH:16][C:15]... | CC(C)(C)OC(=O)N1CCN(c2ccc(C(F)(F)F)cc2C#N)CC1 | [H][H] | null | [Ni] | N | 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 | 0.5 | To a solution 4-(2-cyano-4-trifluoromethyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (150 mg, 0.42 mmol) in NH3/EtOH (2M, 10 mL) was added Raney Nickel (3 mL slurry in water). The atmosphere was exchanged with hydrogen via balloon and the mixture was allowed to stir for 30 min. After this time the mixture w... | CC(C)(C)OC(=O)N1CCN(c2ccc(C(F)(F)F)cc2CN)CC1 | null | 98.1 | null |
256,861 | ord_dataset-30ad5cf6083a45a387b45bebad1a4d65 | null | 1992-01-01T00:10:00 | true | [CH3:1][S:2]([NH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N+:12]([O-])=[C:11]([CH3:17])[CH:10]=[CH:9]2)(=[O:4])=[O:3].C1(C)C=CC(S([Cl:27])(=O)=O)=CC=1>ClCCCl>[Cl:27][CH2:17][C:11]1[CH:10]=[CH:9][C:8]2[C:13](=[CH:14][CH:15]=[C:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH:7]=2)[N:12]=1 | Cc1ccc(S(=O)(=O)Cl)cc1 | Cc1ccc2cc(NS(C)(=O)=O)ccc2[n+]1[O-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClCCCl | null | null | null | null | null | null | null | null | null | null | null | 17 | 6-Methanesulphonamido-2-methylquinoline-1-oxide (1.65 g) and p-toluenesulphonyl chloride (1.72 g) were heated under reflux for 1 hour in 1,2-dichloroethane solution, and the reaction mixture was then stood at room temperature for 17 hours. The reaction mixture was then washed twice with aqueous sodium bicarbonate, drie... | CS(=O)(=O)Nc1ccc2nc(CCl)ccc2c1 | null | null | null |
279,003 | ord_dataset-140fb5527ff24f97bcf0094c5d100120 | null | 1993-01-01T00:11:00 | true | [C:1]1(=[O:11])[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:8]1[C:9]([C:9]2[CH:8]=[CH:7][C:3]3[C:4]([O:6][C:1](=[O:11])[C:2]=3[CH:10]=2)=[O:5])=[CH:10][C:2]2[C:1]([O:6][C:4](=[O:5])[C:3]=2[CH:7]=1)=[O:11] | O=C1OC(=O)c2ccccc21 | null | null | [Pd+2] | CC(=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 | 20 g (135 mmol) of phthalic anhydride was heated at 80° C. for 5 hours in the same manner as in Example 1 except that palladium acetate was omitted. As a result, a BPDA was not formed. | O=C1OC(=O)c2cc(-c3ccc4c(c3)C(=O)OC4=O)ccc21 | null | null | null |
1,629,846 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[S:7])=[CH:4][CH:3]=1.Cl[CH2:12][C:13](=O)[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>C(O)C>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[S:7][CH:12]=[C:13]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:8]=2)=[CH:4][CH:3]=1 | NC(=S)c1ccc(F)cc1 | CCOC(=O)CC(=O)CCl | 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 | To a stirred solution of 4-fluorothiobenzamide (8.94 g, 57.6 mmol) in ethanol (70 mL) was added ethyl 4-chloroacetoacetate (7.8 mL, 58 mmol). The reaction was heated at reflux for 4 hours, treated with an addition aliquot of ethyl 4-chloroacetoacetate (1.0 mL, 7.4 mmol) and refluxed for an additional 3.5 hours. The rea... | CCOC(=O)Cc1csc(-c2ccc(F)cc2)n1 | null | null | null |
112,145 | ord_dataset-5237a168f9214b7ca3db5a1dc3e62d07 | null | 1983-01-01T00:12:00 | true | [F:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[CH3:15][S:16][C:17](SC)=[N:18][C:19]#[N:20]>C(O)C>[C:19]([N:18]=[C:17]([N:10]1[CH2:11][CH2:12][N:7]([CH2:6][C:5]2[CH:13]=[CH:14][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:8][CH2:9]1)[S:16][CH3:15])#[N:20] | CSC(=NC#N)SC | Fc1ccc(CN2CCNCC2)cc1 | 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 28.7 g. (0.1 mole) portion of N-(p-fluorobenzyl)piperazine was dissolved in 25 ml. of ethanol and then added dropwise over 30 minutes to a stirred solution of 14.6 g. (0.1 mole) of dimethyl cyanodithioiminocarbonate in 200 ml. of ethanol. The mixture was refluxed for 6 hours, the evolved gas being led through a sodiu... | CSC(=NC#N)N1CCN(Cc2ccc(F)cc2)CC1 | null | null | null |
1,089,978 | ord_dataset-52a37d876ddb453e86de0c15fa233d29 | null | 2011-01-01T00:09:00 | true | [C:1]1([B:7]([CH:9]([O:16][CH:17]([B:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[OH:25])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:32][CH:33]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:34]O>C(O)C>[... | NC(CO)Cc1ccccc1 | OB(c1ccccc1)C(OC(B(O)c1ccccc1)c1ccccc1)c1ccccc1 | 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 | The entitled compound (6 mg) was obtained by allowing 34 mg of bis(3,3′-(phenylhydroxyboryl)benzyl) ether and 26 mg of 2-amino-3-phenylpropanol to act in 1 mLof ethanol. | NC(COB(c1ccccc1)C(OC(B(OCC(N)Cc1ccccc1)c1ccccc1)c1ccccc1)c1ccccc1)Cc1ccccc1 | null | null | null |
389,856 | ord_dataset-44d518e567bd4c039d77233023f78bb2 | null | 1998-01-01T00:01:00 | true | C([NH:6][NH:7][CH2:8][CH2:9][CH:10]1[NH:14]C(=O)N[C:11]1=[O:16])(OCC)=O.[OH2:17].O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-]>O>[NH2:14][CH:10]([CH2:9][CH2:8][NH:7][NH2:6])[C:11]([OH:16])=[O:17] | CCOC(=O)NNCCC1NC(=O)NC1=O | O | null | [Ba+2] | [OH-] | 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 | Mix 5-[(2-(carbethoxyhydrazino)-ethyl)]-hydantoin (2.3 g, 10 mmol), barium hydroxide octahydrate (18.15 g, 10 mmol) and water (55 mL). Reflux for 12 hours, remove the white solid by filtration, extract the filter cake with boiling water (25 ml) and finally wash with hot water (25 mL). Combine the filtrate and washings,... | NNCCC(N)C(=O)O | null | null | null |
849,080 | ord_dataset-171b840ae6e84e45bab43b987d09f5c7 | null | 2008-01-01T00:11:00 | true | [OH-].[Na+].CO.C([O:7][C:8]([C:10]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:13][S:12][C:11]=1[N:21]1[C:29](=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]1=[O:31])=[O:9])C.Cl>O>[O:30]=[C:29]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22](=[O:31])[N:21]1[C:11]1[S:12][CH:13]=[C:14](... | CCOC(=O)c1c(-c2ccccc2)csc1N1C(=O)c2ccccc2C1=O | null | null | Cl | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CO | O | null | null | null | null | null | null | null | null | null | null | null | To a solution of NaOH (1.4 mmol) in a 1:1 mixture of methanol:H2O (6 mL) was added 2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-4-phenyl-thiophene-3-carboxylic acid ethyl ester (0.7 mmol, Example 1, Part C). The mixture was heated to reflux for 90 min, then diluted with water (12 mL), chilled in an ice bath, and acidified wi... | O=C(O)c1c(-c2ccccc2)csc1N1C(=O)c2ccccc2C1=O | null | 92 | null |
154,602 | ord_dataset-d1c545e3afc447099315419421478aab | null | 1987-01-01T00:03:00 | true | [CH3:1][C:2]1[NH:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[N:6]=1.C(O)(=O)/C=C\C(O)=O.C(N[CH:26]=[N:27][C:28]1[CH:33]=[CH:32][C:31](C2N=C(C)NC=2)=[CH:30][C:29]=1OC)CC>>[C:28]1([NH:27][CH:26]=[N:13][C:10]2[CH:11]=[CH:12][C:7]([C:5]3[N:6]=[C:2]([CH3:1])[NH:3][CH:4]=3)=[CH:8][CH:9]=2)[CH:33]=[CH... | CCCNC=Nc1ccc(-c2c[nH]c(C)n2)cc1OC | Cc1nc(-c2ccc(N)cc2)c[nH]1 | null | O=C(O)/C=C\C(=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 | 25 | 3 | 2-Methyl-4-(4-amino-phenyl)-1H-imidazole (5 g) was added to a solution of ethyl N-phenyl-formamidate (5 g) in acetone (25 ml). After 3 hours of stirring at room temperature, the solid which separated out was filtered off and dried. The product was treated with glacial acetic acid in acetone. The acetate salt which prec... | Cc1nc(-c2ccc(N=CNc3ccccc3)cc2)c[nH]1 | null | null | null |
271,632 | ord_dataset-347c0709d28a44dea43ca42052be4db3 | null | 1993-01-01T00:07:00 | true | [N+:1]([CH3:4])([O-:3])=[O:2].C(NCC)C.[N:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]=[O:17])[CH:11]=1>C(O)C>[N:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]([OH:17])[CH2:4][N+:1]([O-:3])=[O:2])[CH:11]=1 | C[N+](=O)[O-] | O=Cc1cccnc1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCO | CCNCC | null | null | null | null | null | null | null | null | null | 0 | 3 | To a cooled stirring solution of 15 grams (0.25 mol) nitromethane and 0.35 gram (0.005 mol) diethylamine in 26 milliliters of ethanol was added dropwise 10 grams (0.093 mol) 3-pyridine carboxaldehyde. The reaction was stirred for 3 hours at 0° C. then warmed to ambient temperature. Concentration yielded crude 1-(3-pyri... | O=[N+]([O-])CC(O)c1cccnc1 | null | null | null |
956,024 | ord_dataset-ed65749688da45af8a8432967b017729 | null | 2010-01-01T00:05:00 | true | [NH2:1][CH2:2][C@@H:3]([OH:20])[CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=2)[CH2:7][CH2:6]1.[NH2:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][C:23]=1[O:31][CH3:32]>>[NH2:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([NH:1][CH2:2][C@@H:3]([OH:20])[CH2:4][N... | COc1cc(C(=O)O)ccc1N | NC[C@@H](O)CN1CCC(Oc2ccc(Cl)c(Cl)c2)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 | Prepared as described in Example 1 from (2R)-1-amino-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]propan-2-ol (0.1 g) and 4-amino-3-methoxybenzoic acid (0.052 g). Title compound obtained as white solid (0.053 g). | COc1cc(C(=O)NC[C@@H](O)CN2CCC(Oc3ccc(Cl)c(Cl)c3)CC2)ccc1N | null | null | null |
215,062 | ord_dataset-5ebf3d05077a4f7fb91a1cd9bdc504d2 | null | 1990-01-01T00:09:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]([OH:15])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:28][C:29]1[CH:30]=[C:31]([CH2:35][CH2:36][NH2:37])[CH:32]=[CH:33][CH:34]=1>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]([NH:37][CH2:36][CH2:35][C:31]2[CH:32]=[CH:33][CH:34]=... | Cc1cccc(CCN)c1 | COc1ccc(CCC(=O)O)cc1OC | null | O=C(n1ccnc1)n1ccnc1 | 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 | 0.83 | A solution of 3-(3,4-dimethoxyphenyl) propionic acid (21 g, 0.10 mol) and 16.4 g (0.101 mol) of carbonyldiimidazole in dry THF was stirred for 1 h in a flask protected from moisture. To this solution was added 2-(3-methylphenyl)ethylamine (14.2 g, 0.105 mol) and stirring was continued for 50 min. The solvent was evapor... | COc1ccc(CCC(=O)NCCc2cccc(C)c2)cc1OC | null | 87.4 | null |
1,659,389 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | C(N)C1C=CC=CC=1.[F:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[F:18])[CH2:13][NH2:14].[O:19]=[C:20]1[N:24]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)[CH2:23][CH2:22][N:21]1[C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][N:40]=1)[C:35]([O-])=[O:36]>>[F:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[F:18])[CH2:13]... | NCc1ccc(F)c(F)c1 | O=C([O-])c1ccnc(N2CCN(Cc3ccccn3)C2=O)c1 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | NCc1ccccc1 | null | null | null | null | null | null | null | null | null | null | null | null | Following the procedure as described in Example 15, making variations as required to replace benzylamine with 3,4-difluorobenzylamine to react with 2-(2-oxo-3-(pyridin-2-ylmethyl)imidazolidin-1-yl)isonicotinate, N-(3,4-difluorobenzyl)-2-(2-oxo-3-(pyridin-2-ylmethyl)imidazolidin-1-yl)isonicotinamide was obtained as a co... | O=C(NCc1ccc(F)c(F)c1)c1ccnc(N2CCN(Cc3ccccn3)C2=O)c1 | null | 61 | null |
1,660,423 | ord_dataset-42cd9bc5aae3485f9a58f1527bd3abf0 | null | 2015-01-01T00:11:00 | true | [CH3:1][C:2]([S@:5](/[N:7]=[CH:8]/[C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([O:16][CH2:17][C:18]([F:21])([F:20])[F:19])=[CH:11][N:10]=1)=[O:6])([CH3:4])[CH3:3].[CH3:22][Mg]Br.C1COCC1>C(Cl)Cl>[CH3:4][C:2]([S@:5]([NH:7][CH:8]([C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([O:16][CH2:17][C:18]([F:21])([F:19])[F:20])=[CH:11][N:10]=1)[CH3... | C[Mg]Br | Cc1cc(/C=N/[S@](=O)C(C)(C)C)ncc1OCC(F)(F)F | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1CCOC1 | ClCCl | null | null | null | null | null | null | null | null | null | -78 | 1 | To a solution of (R,E)-2-methyl-N-((4-methyl-5-(2,2,2-trifluoroethoxy)pyridin-2-yl)methylene)propane-2-sulfinamide (1.1 g, 3.4 mmol, Step-6) in DCM (50 mL) is added dropwise a solution of methylmagnesium bromide in THF (0.97 M, 7.0 mL, 6.8 mmol) at −78° C. After stirring at −78° C. for 1 h, the reaction is quenched wit... | Cc1cc(C(C)N[S@](=O)C(C)(C)C)ncc1OCC(F)(F)F | null | 94 | null |
325,407 | ord_dataset-fc4cd2699fc04ecbb7c7c831849e6b22 | null | 1996-01-01T00:02:00 | true | [CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([O:11][N:12]=C(C)C)=[C:7]([CH:10]=1)[C:8]#[N:9].Cl.C(=O)([O-])[O-].[Na+].[Na+]>CO>[NH2:9][C:8]1[C:7]2[CH:10]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=2[O:11][N:12]=1 | COc1ccc(ON=C(C)C)c(C#N)c1 | null | null | Cl | O=C([O-])[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 | null | 8 | In 125 ml of dry methanol was dissolved 5-methoxy-2-[[(1-methylethylidene)amino]oxy]benzonitrile (10 g), followed by 125 ml of ethereal hydrochloric acid. The reaction was stirred under nitrogen overnight. The reaction was neutralized with saturated sodium carbonate solution and extracted with EtOAc. The organic layer ... | COc1ccc2onc(N)c2c1 | null | 84.6 | null |
1,369,729 | ord_dataset-d932d1d683704a8bad3d064bcb197acc | null | 2013-01-01T00:11:00 | true | O1[C:5]2([CH2:10][CH2:9][CH:8]([N:11]3[C:16](=[O:17])[C:15]([CH2:18][C:19]4[CH:24]=[CH:23][C:22]([C:25]5[C:26]([C:31]#[N:32])=[CH:27][CH:28]=[CH:29][CH:30]=5)=[CH:21][CH:20]=4)=[C:14]([CH2:33][CH2:34][CH3:35])[N:13]4[N:36]=[C:37]([C:39]([F:42])([F:41])[F:40])[N:38]=[C:12]34)[CH2:7][CH2:6]2)[O:4]CC1.Cl.[OH-].[Na+]>O1CCC... | CCCc1c(Cc2ccc(-c3ccccc3C#N)cc2)c(=O)n(C2CCC3(CC2)OCCO3)c2nc(C(F)(F)F)nn12 | null | null | Cl | [Na+] | [OH-] | 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 | 90 | 20 | To a solution of 4′-{[4-(1,4-dioxaspiro[4.5]dec-8-yl)-5-oxo-7-propyl-2-(trifluoromethyl)-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}biphenyl-2-carbonitrile (7.69 g) in tetrahydrofuran (25 mL) was added 6N hydrochloric acid (25 mL), and the mixture was stirred at 90° C. for 20 hr. The reaction mixture was co... | CCCc1c(Cc2ccc(-c3ccccc3C#N)cc2)c(=O)n(C2CCC(O)CC2)c2nc(C(F)(F)F)nn12 | null | null | null |
1,767,122 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [C:1]([C:5]1[CH:6]=[C:7]([NH2:28])[N:8]([C:10]2[CH:15]=[C:14]([O:16][Si:17]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])[CH:13]=[C:12]([CH3:27])[CH:11]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl[C:32]([O:34][CH2:35][C:36]([Cl:39])([Cl:38])[Cl:37])=[O:33]>C(OCC)(=O)C>[Cl:37][C:... | O=C(Cl)OCC(Cl)(Cl)Cl | Cc1cc(O[Si](C(C)C)(C(C)C)C(C)C)cc(-n2nc(C(C)(C)C)cc2N)c1 | null | [Na+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | CCOC(C)=O | null | null | null | null | null | null | null | null | null | null | null | 0.08 | To a solution of Intermediate 54b (0.73 g, assumed 1.70 mmol) in ethyl acetate (8 mL) was added 1N sodium hydroxide solution (4.5 mL, 4.50 mmol). Stirred for 5 min then 2,2,2-trichloroethyl chloroformate (275 μL, 2.00 mmol) was added and the mixture stirred vigorously at RT for 3.5 h. Diluted with EtOAc, washed with wa... | Cc1cc(O[Si](C(C)C)(C(C)C)C(C)C)cc(-n2nc(C(C)(C)C)cc2NC(=O)OCC(Cl)(Cl)Cl)c1 | null | 103 | null |
319,771 | ord_dataset-0c61835e3a0b4986aabf2b61b708e322 | null | 1995-01-01T00:11:00 | true | [F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]1([C@@H:12](O)[CH3:13])[CH2:11][O:10]1.[F:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[N:23]1[CH:27]=[N:26][NH:25][C:24]1=[O:28]>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]1([O:10][CH2:11]1)[C@H:12]([N:25]1[C:24](=[O:28])[N:23]([C:17]2[CH:... | C[C@H](O)[C@@]1(c2ccc(F)cc2F)CO1 | O=c1[nH]ncn1-c1ccc(F)cc1F | 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 the same manner as in Reference Example 5, starting from 1.36 g of (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol and 1.07 g of 4-(2,4-difluorophenyl)-3(2H,4H)-1,2,4-triazolone, 2-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-methylpropyl]-4-(2,4-difluorophenyl)-3(2H, 4H)-1,2,4-triazolone (1.20 g) was obtained... | C[C@@H](n1ncn(-c2ccc(F)cc2F)c1=O)[C@@]1(c2ccc(F)cc2F)CO1 | null | 58.3 | null |
986,187 | ord_dataset-35b56288528641309a040cc2b6710b61 | null | 2010-01-01T00:08:00 | true | [Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([N:13]3[CH2:18][CH2:17][N:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[F:25])[CH2:15][CH2:14]3)=[O:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.Cl[CH2:27][CH2:28][NH2:29]>>[NH2:29][CH2:28][CH2:27][N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([Cl:1])[CH:10]=2)[C:6]([C:11]([N:13]2[CH2:18][... | O=C(c1c[nH]c2cc(Cl)ccc12)N1CCN(c2ccccc2F)CC1 | NCCCl | 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 general procedure II, the alkylation of (6-chloro-1H-indol-3-yl)-[4-(2-fluoro-phenyl)-piperazin-1-yl]-methanone (preparation described herein), with (commercially available) 2-chloro-ethylamine gave the title compound. | NCCn1cc(C(=O)N2CCN(c3ccccc3F)CC2)c2ccc(Cl)cc21 | null | null | null |
759,817 | ord_dataset-2e58cb8db2bf482bbea23283b7e04488 | null | 2007-01-01T00:03:00 | true | [OH:1][CH:2]([CH3:16])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][NH2:15])=[CH:7][CH:6]=1.Cl.C([NH:22][C:23]([NH:25][C:26]([C:28]1[C:33]([NH2:34])=[N:32][C:31]([NH2:35])=[C:30]([Cl:36])[N:29]=1)=[O:27])=N)CCC>>[ClH:36].[OH:1][CH:2]([CH3:16])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:1... | CC(O)COc1ccc(CCCCN)cc1 | CCCCNC(=N)NC(=O)c1nc(Cl)c(N)nc1N | 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 | Using general procedure Z, 4-[4-(2-hydroxypropyloxy)phenyl]butyl amine was converted into 4-[4-(2-hydroxypropyloxy)phenyl)]butylamidino-3,5-diamino-6-chloropyrazinecarboxamide hydrochloride, m.p. 212–214° C., APCI MS, M/Z=436 [C19H26ClN7O3+H]+. | CC(O)COc1ccc(CCCCNC(=N)NC(=O)c2nc(Cl)c(N)nc2N)cc1 | null | null | null |
1,627,864 | ord_dataset-f0794d5ded7a4d3fab45cc3d7a89ee3d | null | 2015-01-01T00:09:00 | true | [CH3:1][NH:2][C:3]1[C:8]([NH2:9])=[CH:7][C:6]([S:10][C:11]([F:14])([F:13])[F:12])=[CH:5][N:4]=1.[Cl:15][C:16]1[CH:20]=[CH:19][S:18][C:17]=1[C:21](O)=O.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>O.N1C=CC=CC=1>[Cl:15][C:16]1[CH:20]=[CH:19][S:18][C:17]=1[C:21]1[N:2]([CH3:1])[C:3]2=[N:4][CH:5]=[C:6]([S:10][C:11]([F:13])([F:12... | CNc1ncc(SC(F)(F)F)cc1N | O=C(O)c1sccc1Cl | null | CCN=C=NCCCN(C)C | Cl | On1nnc2ccccc21 | null | null | null | null | null | null | null | null | null | null | null | null | null | null | c1ccncc1 | O | null | null | null | null | null | null | null | null | null | 90 | 10 | A mixture of 0.50 g of N2-methyl-5-trifluoromethylthiopyridine-2,3-diamine, 0.44 g of 3-chloro-thiophene-2-carboxylic acid, 0.51 g of EDCI hydrochloride, 30 mg of HOBt and 5 ml of pyridine was stirred at 90° C. for 10 hours. Water was poured into the cooled reaction mixture, and the deposited precipitate was filtered. ... | Cn1c(-c2sccc2Cl)nc2cc(SC(F)(F)F)cnc21 | null | 89.3 | null |
360,385 | ord_dataset-0b24d1f58a024ed7bc2bda95b2430c72 | null | 1997-01-01T00:04:00 | true | [Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18](O)=[O:19])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.[CH2:21]([CH2:28][NH2:29])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18](=[O:19])[NH:29][CH2:28][CH2:21][C:22]3[CH:... | NCCc1ccccc1 | O=C(O)CC1CCc2cc(Br)cc3[nH]c(=O)c(=O)n1c23 | 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 procedure similar to that described in Example 5 was carried out with 9-bromo-5-carboxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (150 mg, 0.44 mmol) and benzylmethylamine (65 μL, 0.5 mmol) to give 170 mg of the title compound (87%): mp 120°~125° C.; 1H NMR (270 MHz, DMSO-d6) δ12.09 and 12.04 (tw... | O=C(CC1CCc2cc(Br)cc3[nH]c(=O)c(=O)n1c23)NCCc1ccccc1 | null | 87.4 | null |
755,394 | ord_dataset-1b0cd79134f0450eaac8396a4f956c30 | null | 2007-01-01T00:02:00 | true | [N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:15](=[O:16])[CH:14]=[CH:13][C:12]2[C:17]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[C:18]([C:20]([O:22]CC)=[O:21])[S:19][C:11]1=2)([O-:3])=[O:2].O.[OH-].[Li+]>O1CCOCC1.O>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:15](=[O:16])[CH:14]=[CH:13][C:12... | CCOC(=O)c1sc2c(ccc(=O)n2-c2ccccc2[N+](=O)[O-])c1-c1ccccc1 | null | null | [Li+] | [OH-] | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | O | null | null | null | null | null | null | null | null | null | null | null | A mixture of the compound of Example 120 (150 mg, 0.357 mmol) and lithium hydroxide monohydrate (30 mg, 0.714 mmol) in dioxane (3 mL) and water (3 mL) was heated under reflux for 1.5 h. The dioxane was removed in vacuo, the aqueous residue acidified (2M HCl) and the precipitate filtered off and dried to give the title ... | O=C(O)c1sc2c(ccc(=O)n2-c2ccccc2[N+](=O)[O-])c1-c1ccccc1 | null | 80 | null |
1,590,264 | ord_dataset-e8c6a25568b64529b960953990e6921f | null | 2015-01-01T00:06:00 | true | C(O[C:6](=O)[N:7]([CH2:9][CH2:10][NH:11][C:12](=[O:43])[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[O:27][C:26]3[C:21](=[N:22][CH:23]=[CH:24][C:25]=3[C:28]3[CH:33]=[CH:32][C:31]([O:34][CH:35]4[CH2:40][CH2:39][O:38][CH2:37][CH2:36]4)=[C:30]([C:41]#[N:42])[CH:29]=3)[CH:20]=2)=[CH:15][CH:14]=1)C)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:41... | CN(CCNC(=O)c1ccc(-c2cc3nccc(-c4ccc(OC5CCOCC5)c(C#N)c4)c3o2)cc1)C(=O)OC(C)(C)C | 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 | 16 | [2-(4-{7-[3-Cyano-4-(tetrahydro-pyran-4-yloxy)-phenyl]-furo[3,2-b]pyridin-2-yl}benzoyl-amino)-ethyl]-methyl-carbamic acid tert-butyl ester (59.0 mg, 0.1 mmol) is dissolved in dichloromethane (1 ml). Trifluoro-acetic acid (1 ml, 12.98 mmol) is added to the solution. The mixture is stirred for 16 h at room temperature. T... | CNCCNC(=O)c1ccc(-c2cc3nccc(-c4ccc(OC5CCOCC5)c(C#N)c4)c3o2)cc1 | null | null | null |
1,535,602 | ord_dataset-8d5c200bca27407ab9febe7598e16458 | null | 2015-01-01T00:01:00 | true | [N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[C:7]2=[O:14])([O-:3])=[O:2].[N+:15]([CH3:18])([O-:17])=[O:16]>O>[OH:14][C:7]1([CH2:18][N+:15]([O-:17])=[O:16])[C:6]2[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[NH:9][C:8]1=[O:13] | C[N+](=O)[O-] | O=C1Nc2ccc([N+](=O)[O-])cc2C1=O | null | null | 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 | 30 | 12 | 5-nitroisatin (0.081 g) and nitromethane (0.15 ml) were added to water (2 ml) and the reaction mixture was vigorously stirred at a temperature of 30° C. for 12 hours. The product was extracted with ethyl acetate and recrystallized with MeOH to afford pure product. | O=C1Nc2ccc([N+](=O)[O-])cc2C1(O)C[N+](=O)[O-] | null | null | null |
913,754 | ord_dataset-c663259b80f947e2a8923796fb0e9a6b | null | 2009-01-01T00:10:00 | true | [CH:1]1([CH2:6][C:7]([NH:9][C:10]2[C:15]([CH3:16])=[CH:14][C:13]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)=[CH:12][C:11]=2[CH3:29])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:30](O)(=O)C.C([BH3-])#N.[Na+].C=O>CO>[CH:1]1([CH2:6][C:7]([NH:9][C:10]2[C:15]([CH3:16])=[CH:14][C:1... | CC(=O)O | Cc1cc(NCc2ccc(C(F)(F)F)cc2)cc(C)c1NC(=O)CC1CCCC1 | null | C=O | [BH3-]C#N | [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 | 1.17 | To 2-cyclopentyl-N-[2,6-dimethyl-4-(4-trifluoromethyl-benzylamino)-phenyl]-acetamide (4k, 150 mg) dissolved in methanol (20 mL) and acetic acid (2 mL) were added sodium cyanoborohydride (175 mg) and formaldehyde (200 uL) and the reaction mixture was stirred at 25° C. for 70 minutes. The reaction was quenched with satur... | Cc1cc(N(C)Cc2ccc(C(F)(F)F)cc2)cc(C)c1NC(=O)CC1CCCC1 | null | 97 | null |
1,121,252 | ord_dataset-285df12e34cd46e993e3c8ebc3a8962a | null | 2012-01-01T00:01:00 | true | ClC1C(NC2C=C(C)NN=2)=NC(N[C@H:9]([C:11]2[N:16]=[CH:15][C:14]([F:17])=[CH:13][N:12]=2)[CH3:10])=NC=1.[BH4-].[Na+].C[OH:28]>>[F:17][C:14]1[CH:13]=[N:12][C:11]([CH:9]([OH:28])[CH3:10])=[N:16][CH:15]=1 | Cc1cc(Nc2nc(N[C@@H](C)c3ncc(F)cn3)ncc2Cl)n[nH]1 | CO | null | [BH4-] | [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 | 0 | 1 | 1-(5-Fluoropyrimidin-2-yl)ethanone (Method 5, 0.77 g) was dissolved in MeOH (15 ml), and the solution was cooled to 0° C. NaBH4 (0.210 g, 5.55 mmol) was added. The mixture was stirred at room temperature for 1 hour and then partitioned between EtOAc and H2O. The organic extract was washed with brine, dried (Na2SO4), fi... | CC(O)c1ncc(F)cn1 | null | 99 | null |
904,957 | ord_dataset-46d216f2c4374ef5b9df90427e2a4cd4 | null | 2009-01-01T00:09:00 | true | Cl[CH2:2][C:3]([C:5]1[C:6]([CH:14]([CH3:16])[CH3:15])=[N:7][N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=12)=O.[NH2:17][C:18]([NH2:20])=[S:19].CC(O)=O>O1CCOCC1>[CH:14]([C:6]1[C:5]([C:3]2[NH:17][C:18](=[S:19])[NH:20][CH:2]=2)=[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][N:8]2[N:7]=1)([CH3:16])[CH3:15] | NC(N)=S | CC(C)c1nn2ccccc2c1C(=O)CCl | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | C1COCCO1 | CC(=O)O | null | null | null | null | null | null | null | null | null | null | null | A mixture of 200 mg (0.63 mmol) of 2-chloro-1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)ethanone, 100 mg of thiourea and 100 μl of HOAc were stirred in 1.5 ml of dioxane at 60-700 C for 30 minutes. 197 mg of 4-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)-1H-imidazole-2(3H)-thione was obtained after workup. Compound 1085. | CC(C)c1nn2ccccc2c1-c1c[nH]c(=S)[nH]1 | null | 121 | null |
1,770,910 | ord_dataset-0b32b90cc77b4a3db47ad263e0bbc1a8 | null | 2016-01-01T00:09:00 | true | [C:1]([O:5][C:6](=[O:24])[N:7]([C@@H:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][C@H:12]1[O:20][CH2:21][O:22][CH3:23])[CH2:8][O:9][CH3:10])([CH3:4])([CH3:3])[CH3:2].[Br:25]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:24])[N:7]([C@@H:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:1... | COCO[C@@H]1Cc2ccccc2[C@H]1N(COC)C(=O)OC(C)(C)C | O=C1CCC(=O)N1Br | null | CC(C)(C#N)N=NC(C)(C)C#N | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | null | ClC(Cl)(Cl)Cl | null | null | null | null | null | null | null | null | null | null | 100 | 0.08 | A solution of 2.75 g of tert-butyl[(1R,2R)-2-(methoxymethoxy)-2,3-dihydro-1H-inden-1-yl](methoxymethyl)carbamate in 55 ml of carbon tetrachloride was heated at an outer temperature of 100° C., and a mixture of 1.53 g of N-bromosuccinimide and 95 mg of 2,2′-azodiisobutyronitrile was added portionwise thereto over 30 min... | COCO[C@@H]1C(Br)c2ccccc2[C@H]1N(COC)C(=O)OC(C)(C)C | null | 29 | null |
646,012 | ord_dataset-c975a50a7600448fabd558f4a94a3e29 | null | 2004-01-01T00:08:00 | true | [CH2:1]([C:3]1[NH:4][C:5](=[O:13])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[N:8]=1)[CH3:2].Br[CH2:15][CH2:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+]>>[CH2:1]([C:3]1[N:4]([CH2:15][CH2:16][O:17][C:18]2[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=2)[C:5](=[O:13... | CCc1nc(C(F)(F)F)cc(=O)[nH]1 | O=Cc1ccc(OCCBr)cc1 | null | O=C([O-])[O-] | [K+] | 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 (138 mg, 40%) was prepared from 2-ethyl-4-trifluoromethyl-1,6-dihydro-6-pyrimidone (200 mg, 1.04 mmol) and 4-[2-bromoethoxy]benzaldehyde (238.5 mg, 1.04 mmol) in presence of K2CO3 (287.5 mg, 2.08 mmol) as base by a similar procedure to that described in preparation 1. | CCc1nc(C(F)(F)F)cc(=O)n1CCOc1ccc(C=O)cc1 | null | 39 | null |
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