p-Toluenesulfonic acid → N-(4-{4-amino-7-[(1E)-3-oxoprop-1-enyl]thieno[3,2-c]pyridin-3-yl}-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamide

HRID 1270860

반응식

HRID 1270860 반응식
[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]4[N:21]([CH3:29])[C:22]5[C:27]([CH:28]=4)=[CH:26][CH:25]=[CH:24][CH:23]=5)=[O:19])=[C:13]([O:30][CH3:31])[CH:12]=3)=[CH:9][S:10][C:6]=2[C:5](/[CH:32]=[CH:33]/[CH:34](OCC)[O:35]CC)=[CH:4][N:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O.O>[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]4[N:21]([CH3:29])[C:22]5[C:27]([CH:28]=4)=[CH:26][CH:25]=[CH:24][CH:23]=5)=[O:19])=[C:13]([O:30][CH3:31])[CH:12]=3)=[CH:9][S:10][C:6]=2[C:5](/[CH:32]=[CH:33]/[CH:34]=[O:35])=[CH:4][N:3]=1

참가 물질

5

반응물 2

HCID 6101p-Toluenesulfonic acidHCID 18450992n-(4-{4-Amino-7-[(1e)-3,3-diethoxy-1-propenyl]thieno[3,2-c]pyridin-3-yl}-2-methoxyphenyl)-1-methyl-1h-indole-2-carboxamide

생성물 1

HCID 18451050N-(4-{4-amino-7-[(1E)-3-oxoprop-1-enyl]thieno[3,2-c]pyridin-3-yl}-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamide수율 99.7%

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매

실험 절차

A mixture of Example 176B (90 mg, 0.16 mmol) in acetone (9 mL) and water (1 mL) was treated with p-toluenesulfonic acid (5 mg, 0.016 mmol) then stirred for 30 minutes. The solvent was evaporated under reduced pressure then the residue was partitioned between dichloromethane and water. The organic layer was concentrated and the residue was purified by flash chromatography on silica gel to provide the desired product (77 mg). 1H NMR (DMSO-d6, 400 MHz) δ 9.67 (d, 1H), 9.52 (s, 1H), 8.34 (s, 1H), 8.03 (d, 1H), 7.91 (d, 1H), 7.75 (s, 1H), 7.70 (d, 1H), 7.32 (m, 2H), 7.25 (s, 1H), 7.10 (m, 3H), 6.69 (m, 1H), 4.04 (s, 3H), 3.92 (s, 3H); MS m/e 483.3.

후처리

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was partitioned between dichloromethane and water
  3. concentrationThe organic layer was concentrated
  4. customthe residue was purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-4a08f8add446474dad136c53f9f4f976
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07202363B2

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