(R)-(+)-beta-Methylphenethylamine → 1-(4-(methylamino)-6-{[(2R)-2-phenylpropyl]amino}-1,3,5-triazin-2-yl)-N-{[2-(trifluoromethyl)phenyl]methyl}-4-piperidinecarboxamide

HRID 1678412Notes

Reaction equation

HRID 1678412 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH3:9])[N:5]=[C:4]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]([NH:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([F:29])([F:28])[F:27])=[O:17])[CH2:12][CH2:11]2)[N:3]=1.[C:30]1([C@@H:36]([CH3:39])[CH2:37][NH2:38])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[CH3:9][NH:8][C:6]1[N:7]=[C:2]([NH:38][CH2:37][C@@H:36]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH3:39])[N:3]=[C:4]([N:10]2[CH2:11][CH2:12][CH:13]([C:16]([NH:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([F:29])([F:27])[F:28])=[O:17])[CH2:14][CH2:15]2)[N:5]=1

Participants

3

Reactant 2

HCID 1547949(R)-(+)-beta-MethylphenethylamineHCID 866443121-[4-chloro-6-(methylamino)-1,3,5-triazin-2-yl]-N-{[-(trifluoromethyl)phenyl]methyl}-4-piperidinecarboxamide

Product 1

HCID 252274551-(4-(methylamino)-6-{[(2R)-2-phenylpropyl]amino}-1,3,5-triazin-2-yl)-N-{[2-(trifluoromethyl)phenyl]methyl}-4-piperidinecarboxamide

Conditions

Temperature
80 °C

Procedure

Approximately half of the suspension prepared in step c was treated with (2R)-2-phenylpropylamine (1.16 mL, 8.14 mmol, 10.0 equiv). After heating to 80° C., the solvents were removed in vacuo, and the residue was purified by reverse-phase HPLC (Sunfire, 35-60% CH3CN/H2O, 0.1% TFA, 12 min) to afford 156 mg of the title compound. MS (ES+): m/e 528.1 [M+H]+.

Workup

  1. customthe solvents were removed in vacuo
  2. customthe residue was purified by reverse-phase HPLC (Sunfire, 35-60% CH3CN/H2O, 0.1% TFA, 12 min)

Sources & evidence

ORD record
ord-556d0c9350884c318a6e9232385e2a45
Source dataset
uspto-grants-2011_08
Patent number
US08008483B2

Reaction notes

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