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Cyano-borohydride → 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 2061832
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HRID 2061832 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][CH: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][CH: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 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 498716Cyano-borohydrideHCID 17998884Morpholin-4-yl-acetaldehyde monohydrate hydrochlorideHCID 59617720Ethyl 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 59415909Ethyl 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
수율 37.4%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A vial was charged with 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 239, 700 mg, 1.14 mmol), morpholin-4-yl-acetaldehyde monohydrate hydrochloride (260 mg, 1.39 mmol) and methanol (10 mL). MP-cyanoborohydride beads (730 mg, 1.71 mmol) were added and the resulting mixture was allowed to stir at room temperature overnight. The reaction went to completion based on LC. The mixture was filtered and the beads were washed with methanol. The filtrate was concentrated under reduced pressure and purified by Analogix SF15-24 g column eluting with dichloromethane/methanol system to give a light yellow solid (310 mg, 37.4%).

후처리

  1. additionwere added
  2. filtrationThe mixture was filtered
  3. washthe beads were washed with methanol
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. custompurified by Analogix SF15-24 g column
  6. washeluting with dichloromethane/methanol system

출처 및 근거

ORD 기록
ord-eed7755e021e4797b49b374f78e176ef
출처 데이터셋
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08283361B2

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