Benzylamine → HCID 178482253, compound

HRID 1671777Notes

Reaction equation

HRID 1671777 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH:8][CH3:9])[N:5]=[C:4]([NH:10][C@@H:11]2[CH2:16][CH2:15][C@H:14]([C:17]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]([F:30])([F:29])[F:28])=[O:18])[CH2:13][CH2:12]2)[N:3]=1.[CH2:31]([NH2:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CC(O)C.Cl>[CH3:9][NH:8][C:6]1[CH:7]=[C:2]([NH:38][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:3]=[C:4]([NH:10][C@@H:11]2[CH2:16][CH2:15][C@H:14]([C:17]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]([F:29])([F:28])[F:30])=[O:18])[CH2:13][CH2:12]2)[N:5]=1

Participants

5

Reactant 2

HCID 7504BenzylamineHCID 178482188HCID 178482188, compound

Product 1

HCID 178482253HCID 178482253, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 3776IsopropanolSolvent

Procedure

To a solution of cis-4-{[4-chloro-6-(methylamino)-2-pyrimidinyl]amino}-N-{[2-(trifluoromethyl)phenyl]methyl}cyclohexanecarboxamide (50.0 mg, 0.11 mmol) and benzylamine (59.0 mg, 0.55 mmol) in 2-propanol (3 mL) was added one drop of concentrated HCl. The mixture was irradiated in the microwave for 3 hours at 170° C., at which time LCMS indicated the formation of the desired product. The crude reaction mixture was filtered and purified directly by preparative HPLC (gradient; 30-80% CH3CN:H2O (0.1% TFA)), to afford the title compound (30 mg, 0.58 mmol, 52%). MS (ES+) m/e 513 [M+H]+.

Workup

  1. customThe mixture was irradiated in the microwave for 3 hours at 170° C., at which time LCMS

Sources & evidence

ORD record
ord-4a8bb7aeacb540988b938968df4d3b52
Source dataset
uspto-grants-2011_08
Patent number
US07994317B2

Reaction notes

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