Lithium Hydroxide → HCID 46833516, compound

HRID 1510286Notes

Reaction equation

HRID 1510286 reaction equation
C([O:3][C:4](=[O:41])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([NH:23][C:24]([C:26]4[N:27]=[C:28]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)[O:29][C:30]=4[C:31]([F:34])([F:33])[F:32])=[O:25])=[CH:19][N:18]=3)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)C.[Li+].[OH-]>C1COCC1.CO>[C:35]1([C:28]2[O:29][C:30]([C:31]([F:32])([F:34])[F:33])=[C:26]([C:24]([NH:23][C:20]3[CH:21]=[CH:22][C:17]([N:14]4[CH2:13][CH2:12][N:11]([C:8]5[CH:9]=[CH:10][C:5]([C:4]([OH:41])=[O:3])=[CH:6][CH:7]=5)[CH2:16][CH2:15]4)=[N:18][CH:19]=3)=[O:25])[N:27]=2)[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 46832612HCID 46832612, compound

Product 1

HCID 46833516HCID 46833516, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To 4-(4-{5-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-pyridin-2-yl}-piperazin-1-yl)-benzoic acid ethyl ester (130 mg, 0.23 mmol) dissolved in a 1:1 mixture of THF/methanol (2 mL) was added 1N LiOH (2.60 mL, 2.60 mmol). The mixture was stirred at rt overnight. The crude mixture was acidified to pH=1 and purified by HPLC to give 4-(4-{5-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-pyridin-2-yl}-piperazin-1-yl)-benzoic acid. The NMR spectrum obtained on the sample is compatible with its structure. LCMS calcd for C27H22F3N5O4 (m/e) 537, obsd 538 (M+H).

Workup

  1. custompurified by HPLC

Sources & evidence

ORD record
ord-4fb437bda3974d8db1c5b0c976b47f5b
Source dataset
uspto-grants-2012_07
Patent number
US08211914B2

Reaction notes

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