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Sodium Hydroxide → sodium (1S,4R)-4-hydroxy-2,2-dimethyl-4-[5-(3-methyl-5-([4-(trifluoromethyl)pyrimidin-2-yl]amino) phenyl)-1,3-thiazol-2-yl]-cyclohexanecarboxylate

HRID 1040046
Notes
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Reaction equation

HRID 1040046 reaction equation
[OH:1][C@:2]1([C:13]2[S:14][C:15]([C:18]3[CH:23]=[C:22]([NH:24][C:25]4[N:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][N:26]=4)[CH:21]=[C:20]([CH3:35])[CH:19]=3)=[CH:16][N:17]=2)[CH2:7][CH2:6][C@H:5]([C:8]([OH:10])=[O:9])[C:4]([CH3:12])([CH3:11])[CH2:3]1.[OH-].[Na+:37]>C(#N)C.O>[OH:1][C@:2]1([C:13]2[S:14][C:15]([C:18]3[CH:23]=[C:22]([NH:24][C:25]4[N:30]=[C:29]([C:31]([F:33])([F:34])[F:32])[CH:28]=[CH:27][N:26]=4)[CH:21]=[C:20]([CH3:35])[CH:19]=3)=[CH:16][N:17]=2)[CH2:7][CH2:6][C@H:5]([C:8]([O-:10])=[O:9])[C:4]([CH3:11])([CH3:12])[CH2:3]1.[Na+:37]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53251506(1S,4R)-4-hydroxy-2,2-dimethyl-4-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]cyclohexanecarboxylic acid

Product 1

HCID 67432894sodium (1S,4R)-4-hydroxy-2,2-dimethyl-4-[5-(3-methyl-5-([4-(trifluoromethyl)pyrimidin-2-yl]amino) phenyl)-1,3-thiazol-2-yl]-cyclohexanecarboxylate

Reagents, catalysts & solvents 2

HCID 962Water
Solvent
2×
HCID 6342AcetonitrileSolvent

Conditions

Temperature
35 °C

Procedure

(1S,4R)-4-Hydroxy-2,2-dimethyl-4-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}-phenyl)-1,3-thiazol-2-yl]cyclohexanecarboxylic acid (9.8 mg, 0.019 mmol) was dissolved in acetonitrile (20 μL) and water (20 μL). Sodium hydroxide (19 μL, 0.019 mmol) was added, and the mixture was heated to 35° C. for 10 min. The mixture was allowed to cool to rt, diluted with water, froze to a solid, and lyophilized to dryness to afford sodium (1S,4R)-4-hydroxy-2,2-dim ethyl-4-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]-cyclohexanecarboxylate.

Workup

  1. temperatureto cool to rt

Sources & evidence

ORD record
ord-316ff4d2aa4b43ea8cf91702ec7caf98
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08551984B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes