Methanol → HCID 118092590, compound

HRID 2207375Notes

Reaction equation

HRID 2207375 reaction equation
[OH-].[K+].CO.[OH:5][C:6]1([C:14]2[CH:15]=[N:16][CH:17]=[C:18]([C:20]3[CH:25]=[C:24]([NH:26][C:27]4[N:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][N:28]=4)[CH:23]=[C:22]([CH3:37])[CH:21]=3)[CH:19]=2)[CH2:10][CH2:9][CH:8]([C:11]([O-:13])=[O:12])[CH2:7]1>Cl>[OH:5][C:6]1([C:14]2[CH:15]=[N:16][CH:17]=[C:18]([C:20]3[CH:25]=[C:24]([NH:26][C:27]4[N:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][N:28]=4)[CH:23]=[C:22]([CH3:37])[CH:21]=3)[CH:19]=2)[CH2:10][CH2:9][CH:8]([C:11]([OH:13])=[O:12])[CH2:7]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 131735897HCID 131735897, compound

Product 1

HCID 118092590HCID 118092590, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of KOH in MeOH (1 M, 2 mL, 2.00 mmol) was added to the 3-hydroxy-3-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-3-yl]cyclopentanecarboxylate (60 mg, 0.123 mmol). The reaction mixture was stirred at room temperature, overnight, diluted with 2N HCl and extracted with DCM (3×). The combined organic layers were dried under reduced pressure to give 3-hydroxy-3-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-3-yl]cyclopentanecarboxylic acid. MS ESI calc'd for C23H22F3N4O3 [M+H]+ 459. found 459. 1H NMR (500 MHz, MeOD) δ 9.01 (s, 1H), 8.92 (d, J=6.0 Hz, 1H), 8.74 (d, J=5.0 Hz, 1H), 8.19 (s, 1H), 7.63 (s, 2H), 7.35 (s, 1H), 7.17 (d, J=5.0 Hz, 1H), 2.51-2.00 (m, 7H), 1.19 (s, 3H).

Workup

  1. extractionextracted with DCM (3×)
  2. customThe combined organic layers were dried under reduced pressure

Sources & evidence

ORD record
ord-d6874e8a7aea4a75a43da974ea5eb9f6
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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