Methanol → N-{4-[4-amino-7-(3-hydroxypropyl)thieno[3,2-c]pyridin-3-yl]-2-methoxyphenyl}-1H-indole-2-carboxamide

HRID 17249ノート

反応式

HRID 17249 の反応式
[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](C)[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]/[CH2:34][OH:35])=[CH:4][N:3]=1.CO.[BH4-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=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[NH:21][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]([CH2:32][CH2:33][CH2:34][OH:35])=[CH:4][N:3]=1

参加物

6

反応物 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 4311764Sodium borohydrideHCID 18451044trans-N-(4-(4-amino-7-(3-hydroxyprop-1-enyl)thieno[3,2-c]pyridin-3-yl)-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamide

生成物 1

HCID 68677946N-{4-[4-amino-7-(3-hydroxypropyl)thieno[3,2-c]pyridin-3-yl]-2-methoxyphenyl}-1H-indole-2-carboxamide収率 19%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

N-(4-{4-Amino-7-[(1E)-3-hydroxyprop-1-enyl]thieno[3,2-c]pyridin-3-yl}-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamide (110 mg, 0.228 mmol), methanol (2 mL) and N,N-dimethylforamide (2 mL) was added sodium borohydride (26.9 mg, 0.684 mmol) under an atmosphere of nitrogen. Mixture stirred for 30 minutes at room temperature after which it was treated with 1M sodium carbonate (5 mL) and extracted with dichloromethane (3×5 mL). The organic layer was separated, dried over magnesium sulfate, and filtered, and the solvent was removed under reduced pressure. The product was purified via flash chromatography to furnish the title compound as a pale yellow powder (21.1 mg, 0.0434 mmol): LCMS (Thermoquest AQA single-quad MS, Genesis C18 column, 3 mm particle size, 33×4.6 mm; 70% 50 mM ammonium Acetate in Water to 95% Acetonitrile over 4.5 min, 0.8 mL/min): MH+=487 RT=3.23 minutes; 1H NMR (DMSO-d6, 400 MHz) δ 9.51 (1 H), 7.99 (1 H), 7.70 (2 H), 7.60 (1 H), 7.55(1 H), 7.32-7.35 (2 H), 7.21 (1 H), 7.15 (1 H), 7.07 (1 H), 5.34 (2 H), 4.04 (3 H), 3.91 (3 H), 3.47 (2 H), 2.75 (2 H), 1.83 (4 H).

後処理

  1. extractionextracted with dichloromethane (3×5 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customThe product was purified via flash chromatography

出典と根拠

ORDレコード
ord-f00e7a8640ca413f917e7c03b3e832f9
出典データセット
uspto-grants-2010_06
特許番号
US07737160B2

反応ノート

読み込み中…