Lithium Hydroxide → HCID 178525485, compound

HRID 1819486Notes

Reaction equation

HRID 1819486 reaction equation
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]

Participants

5

Reactant 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

Product 1

HCID 178525485HCID 178525485, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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)+].

Workup

  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)+]

Sources & evidence

ORD record
ord-d351c7e376044cce9b4d111c5bd8a7e4
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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