Tetrahydrofuran → HCID 71293676, 화합물

HRID 1402554노트

반응식

HRID 1402554 반응식
[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]

참가 물질

8

반응물 5

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 2733200methyl L-prolinate hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 71541978HCID 71541978, 화합물

생성물 1

HCID 71293676HCID 71293676, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-5b09c82262504ab6a8e3d96b8555a759
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08906944B2

반응 노트

불러오는 중…