Sodium Hydroxide → HCID 178482188, compound

HRID 1671776Notes

Reaction equation

HRID 1671776 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH3:9])[CH:5]=[C:4]([Cl:10])[N:3]=1.[NH2:11][C@@H:12]1[CH2:17][CH2:16][C@H:15]([C:18]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]([F:31])([F:30])[F:29])=[O:19])[CH2:14][CH2:13]1.FC(F)(F)C([O-])=O.[OH-].[Na+]>CC#N.O>[Cl:10][C:4]1[CH:5]=[C:6]([NH:8][CH3:9])[N:7]=[C:2]([NH:11][C@@H:12]2[CH2:13][CH2:14][C@H:15]([C:18]([NH:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]([F:29])([F:30])[F:31])=[O:19])[CH2:16][CH2:17]2)[N:3]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 84468TrifluoroacetateHCID 155636442,6-Dichloro-N-methylpyrimidin-4-amineHCID 178511564HCID 178511564, compound2×

Product 1

HCID 178482188HCID 178482188, compound

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a solution of 2,6-dichloro-N-methyl-4-pyrimidinamine (360 mg, 2.0 mmol) and cis-4-amino-N-{[2-(trifluoromethyl)phenyl]methyl}cyclohexanecarboxamide (Intermediate 1) trifluoroacetate (829 mg, 2.0 mmol), in MeCN/H2O (1:1, 5 mL) was added 1N NaOH solution until a pH of 12 was achieved. The mixture was irradiated in the microwave for 4 hours at 170° C., at which time LCMS indicated the formation of the desired product. The reaction mixture was extracted with EtOAc (2×50 mL), washed with water (2×50 mL), dried (Na2SO4), and concentrated to afford a waxy solid. The crude material was purified by column chromatography (Gradient from 0-5% MeOH in CH2Cl2) to afford 300 mg (0.68 mmol, 34%) of a colorless wax MS (ES+) m/e 442 [M+H]+. Regiochemistry was verified by 2D NMR analysis.

Workup

  1. customThe mixture was irradiated in the microwave for 4 hours at 170° C., at which time LCMS

Sources & evidence

ORD record
ord-bd02ffef745d4d5883d93813681746e3
Source dataset
uspto-grants-2011_08
Patent number
US07994317B2

Reaction notes

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