Water → HCID 68725893, compound

HRID 2093617Notes

Reaction equation

HRID 2093617 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([NH:13][CH2:14][CH:15]2[CH2:20][CH2:19][N:18]([C:21]3[N:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:23][N:22]=3)[CH2:17][CH2:16]2)=[O:12])=[CH:7][N:6]=1)=[O:4].O.[OH-].[Li+]>O1CCCC1.CO>[F:30][C:27]([F:28])([F:29])[C:25]1[CH:24]=[CH:23][N:22]=[C:21]([N:18]2[CH2:17][CH2:16][CH:15]([CH2:14][NH:13][C:11]([C:8]3[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][CH:7]=3)=[O:12])[CH2:20][CH2:19]2)[N:26]=1

Participants

6

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 68727626HCID 68727626, compound

Product 1

HCID 68725893HCID 68725893, compoundYield 87.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of methyl-5-{[({1-[4-(trifluoromethyl)pyrimidin-2-yl]piperidin-4-yl}methyl)amino]carbonyl}pyridine-2-carboxylate (272 mg, 0.643 mmol) in tetrahydrofuran, methanol, and water (5 ml, in a ratio of 3:2:1, respectively) was added lithium hydroxide (108 mg, 2.57 mmol). The reaction was stirred at ambient temperature for 18 h and then concentrated in vacuo to afford the title compound as a white solid (230 mg). Mass spectrum (ESI) 410 (M+1). 1H NMR (500 MHz, CD3OD) δ 8.96 (s, 1H), 8.54 (d, 1H, J=4.8 Hz), 8.24 (d, 1H, J=8.3 Hz), 8.05 (d, 1H, J=8 Hz), 6.81 (d, 1H, J=4.8 Hz), 4.70-5.0 (m, 2H), 2.94-3.01 (m, 2H), 1.97-2.03 (m, 1H), 1.88 (d, 2H, J=12.8 Hz), 1.21-1.34 (m, 4H).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a93b604e3878489cbc6942cf6517a12d
Source dataset
uspto-grants-2013_05
Patent number
US08445480B2

Reaction notes

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