Cyano-borohydride → (S)-ethyl 6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1-((1-(2-morpholinoethyl)pyrrolidin-3-yl)methyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 2061828노트

반응식

HRID 2061828 반응식
[CH2:1]([NH:3][C:4](=[O:43])[NH:5][C:6]1[N:11]=[CH:10][C:9]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]([CH2:22][C@H:23]2[CH2:27][CH2:26][NH:25][CH2:24]2)[CH:17]=[C:16]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:15]3=[O:33])=[C:8]([C:34]2[S:35][CH:36]=[C:37]([C:39]([F:42])([F:41])[F:40])[N:38]=2)[CH:7]=1)[CH3:2].Cl.O.[N:46]1([CH2:52][CH:53]=O)[CH2:51][CH2:50][O:49][CH2:48][CH2:47]1.C([BH3-])#N>CO>[CH2:1]([NH:3][C:4](=[O:43])[NH:5][C:6]1[N:11]=[CH:10][C:9]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]([CH2:22][C@H:23]2[CH2:27][CH2:26][N:25]([CH2:53][CH2:52][N:46]4[CH2:51][CH2:50][O:49][CH2:48][CH2:47]4)[CH2:24]2)[CH:17]=[C:16]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:15]3=[O:33])=[C:8]([C:34]2[S:35][CH:36]=[C:37]([C:39]([F:42])([F:41])[F:40])[N:38]=2)[CH:7]=1)[CH3:2]

참가 물질

5

반응물 3

HCID 498716Cyano-borohydrideHCID 17998884Morpholin-4-yl-acetaldehyde monohydrate hydrochlorideHCID 86643626(S)-ethyl 6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-4-oxo-1-(pyrrolidin-3-ylmethyl)-1,4-dihydroquinoline-3-carboxylate

생성물 1

HCID 86643629(S)-ethyl 6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1-((1-(2-morpholinoethyl)pyrrolidin-3-yl)methyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate수율 45.8%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A vial was charged with (S)-ethyl 6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-4-oxo-1-(pyrrolidin-3-ylmethyl)-1,4-dihydroquinoline-3-carboxylate (Example 234, 800 mg, 1.3 mmol) and morpholin-4-yl-acetaldehyde monohydrate hydrochloride (270 mg, 1.47 mmol) in methanol (10 mL). MP-cyanoborohydride (850 mg, 2.0 mmol) beads were added and the resulting mixture was allowed to stir at room temperature overnight. The mixture was filtered and the beads were washed with more methanol. The filtrate was concentrated and purified by Analogix SF15-24 g in DCM/methanol system to give a light yellow solid (380 mg, 45.8%).

후처리

  1. filtrationThe mixture was filtered
  2. washthe beads were washed with more methanol
  3. concentrationThe filtrate was concentrated
  4. custompurified by Analogix SF15-24 g in DCM/methanol system

출처 및 근거

ORD 기록
ord-1747e160aa52456c9297b8e40a26b816
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08283361B2

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