Tetrahydrofuran → HCID 71293676、化合物

HRID 1402554ノート

反応式

HRID 1402554 の反応式
[F:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([C:13]3[NH:17][CH:16]=[C:15]([C:18]([NH:20][CH2:21][CH2:22][CH:23]=O)=[O:19])[CH:14]=3)[CH:8]=2)=[CH:4][C:3]=1[NH:27][C:28]([C:30]1[O:31][CH:32]=[CH:33][C:34]=1[CH3:35])=[O:29].Cl.[CH3:37][O:38][C:39](=[O:45])[C@@H:40]1[CH2:44][CH2:43][CH2:42][NH:41]1.C(N(CC)CC)C.C([BH3-])#N.[Na+].C1COCC1>CN(C=O)C.O>[F:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([C:13]3[NH:17][CH:16]=[C:15]([C:18]([NH:20][CH2:21][CH2:22][CH2:23][N:41]4[CH2:42][CH2:43][CH2:44][CH:40]4[C:39]([O:38][CH3:37])=[O:45])=[O:19])[CH:14]=3)[CH:8]=2)=[CH:4][C:3]=1[NH:27][C:28]([C:30]1[O:31][CH:32]=[CH:33][C:34]=1[CH3:35])=[O:29]

参加物

8

反応物 5

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 2733200methyl L-prolinate hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 71541978HCID 71541978、化合物

生成物 1

HCID 71293676HCID 71293676、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of 5-(4-{4-fluoro-3-[(3-methyl-2-furoyl)amino]phenoxy}pyridin-2-yl)-N-(3-oxopropyl)-1H-pyrrole-3-carboxamide (140 mg, 0.29 mmol) in 10 ml of anhydrous DMF were added L-proline methyl ester hydrochloride (96 mg, 0.58 mmol) and triethylamine (58 mg, 0.58 mmol). The mixture was stirred at room temperature for 30 minutes, followed by addition of 1M sodium cyanoborohydride solution in THF (0.60 ml, 0.60 mmol) and stirring was continued for another 30 minutes. The mixture was poured into 100 ml of water. The precipitates were filtered, washed with water and dried to give the crude, which was purified by silica gel flash chromatography eluting with 5% of MeOH in CHCl3 to give methyl 1-[3-({[5-(4-{4-fluoro-3-[(3-methyl-2-furoyl)amino]phenoxy}pyridin-2-yl)-1H-pyrrol-3-yl]carbonyl}amino)propyl]pyrrolidine-2-carboxylate as light beige solid. Yield: 70 mg, 40%.

後処理

  1. stirringstirring
  2. waitwas continued for another 30 minutes
  3. filtrationThe precipitates were filtered
  4. washwashed with water
  5. customdried
  6. customto give the crude, which
  7. customwas purified by silica gel flash chromatography
  8. washeluting with 5% of MeOH in CHCl3

出典と根拠

ORDレコード
ord-5b09c82262504ab6a8e3d96b8555a759
出典データセット
uspto-grants-2014_12
特許番号
US08906944B2

反応ノート

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