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Lithium Hydroxide → HCID 178525485, 화합물

HRID 1819486
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HRID 1819486 반응식
C[O:2][C:3](=[O:38])[CH2:4][CH2:5][CH2:6][NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]2[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][N:19]=[C:18]([NH:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[O:33][C:34]([F:37])([F:36])[F:35])[N:17]=2)[CH2:10][CH2:9]1.CO.O.[Li+].[OH-]>CO>[N+:22]([C:21]1[C:16]([NH:15][CH2:14][C@H:11]2[CH2:12][CH2:13][C@H:8]([NH:7][CH2:6][CH2:5][CH2:4][C:3]([OH:38])=[O:2])[CH2:9][CH2:10]2)=[N:17][C:18]([NH:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][C:34]([F:37])([F:36])[F:35])=[N:19][CH:20]=1)([O-:24])=[O:23]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 3939Lithium HydroxideHCID 22242641Methanol--water (1/1)HCID 578856074-(4-{[5-Nitro-2-(2-trifluoromethoxy-benzylamino)-pyrimidin-4-ylamino]-methyl}-cyclohexylamino)-butyric acid methyl ester

생성물 1

HCID 178525485HCID 178525485, 화합물

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 4-(4-{[5-nitro-2-(2-trifluoromethoxy-benzylamino)-pyrimidin-4-ylamino]-methyl}-cyclohexylamino)-butyric acid methyl ester (39 mg, 0.072 mmol) in 6:1 MeOH/water (0.7 mL) was added LiOH (9 mg, 0.375 mmol) and the mixture stirred at room temperature overnight. The resulting suspension was diluted with MeOH (1 mL) and stirred at room temperature for a further 2 h. The reaction mixture was concentrated in vacuo and the remaining aqueous residue treated with 2 N HCl until the mixture reached pH 5-6. The resulting solid was filtered and washed with water. The material was subjected to semi-preparative to separate the title compound [7 mg, 13%, m/z 527 (M+1)+] and 1-(trans-4-{[(5-nitro-2-{[2-(trifluoromethoxy)benzyl]amino}pyrimidin-4-yl)amino]methyl}cyclohexyl)pyrrolidin-2-one [15 mg, 41%, m/z 509 (M+1)+].

후처리

  1. stirringstirred at room temperature for a further 2 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionthe remaining aqueous residue treated with 2 N HCl until the mixture
  4. filtrationThe resulting solid was filtered
  5. washwashed with water
  6. customto separate the title compound [7 mg, 13%, m/z 527 (M+1)+] and 1-(trans-4-{[(5-nitro-2-{[2-(trifluoromethoxy)benzyl]amino}pyrimidin-4-yl)amino]methyl}cyclohexyl)pyrrolidin-2-one [15 mg, 41%, m/z 509 (M+1)+]

출처 및 근거

ORD 기록
ord-d351c7e376044cce9b4d111c5bd8a7e4
출처 데이터셋
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07601714B2

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