Lithium Hydroxide → HCID 178524360, compound

HRID 1819482Notes

Reaction equation

HRID 1819482 reaction equation
C[O:2][C:3](=[O:42])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][NH:11][CH:12]2[CH2:17][CH2:16][CH:15]([CH2:18][NH:19][C:20]3[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][N:23]=[C:22]([NH:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=4[O:37][C:38]([F:41])([F:40])[F:39])[N:21]=3)[CH2:14][CH2:13]2)[CH:5]=1.[Li+].[OH-]>O.CO>[N+:26]([C:25]1[C:20]([NH:19][CH2:18][C@H:15]2[CH2:16][CH2:17][C@H:12]([NH:11][CH2:10][C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:42])=[O:2])[CH2:13][CH2:14]2)=[N:21][C:22]([NH:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[O:37][C:38]([F:41])([F:40])[F:39])=[N:23][CH:24]=1)([O-:28])=[O:27]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 598456853-[(4-{[5-Nitro-2-(2-trifluoromethoxy-benzylamino)-pyrimidin-4-ylamino]-methyl}-cyclohexylamino)-methyl]-benzoic acid methyl ester

Product 1

HCID 178524360HCID 178524360, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3-[(4-{[5-nitro-2-(2-trifluoromethoxy-benzylamino)-pyrimidin-4-ylamino]-methyl}-cyclohexylamino)-methyl]-benzoic acid methyl ester (75 mg, 0.13 mmol), LiOH (30 mg, 1.29 mmol) and water (3 drops) in MeOH (2 mL) was heated at 50° C. for 18 h. The reaction mixture was concentrated in vacuo then taken up in water and EtOAc. Dilute HCl was added until the aqueous phase reached pH 6. The solid that precipitated was isolated by filtration to afford the target compound (20 mg, 30%) as a white solid, m/z 575 (M+1)+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionDilute HCl was added until the aqueous phase
  3. customThe solid that precipitated
  4. customwas isolated by filtration

Sources & evidence

ORD record
ord-26d6b13705e84d278b7e9b2807522777
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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