Formic Acid → HCID 89442639, compound

HRID 2284052Notes

Reaction equation

HRID 2284052 reaction equation
F[C:2](F)(F)C(O)=O.[NH2:8][C:9]1[C:14]([C:15]([NH2:17])=[O:16])=[C:13]([N:18]2[CH2:23][CH2:22][CH:21]([C:24]3[N:25]([CH2:40][CH:41]4[CH2:44][NH:43][CH2:42]4)[CH:26]=[C:27]([C:29]4[CH:34]=[CH:33][C:32]([F:35])=[C:31]([C:36]([F:39])([F:38])[F:37])[CH:30]=4)[N:28]=3)[CH2:20][CH2:19]2)[N:12]=[CH:11][N:10]=1.C(O)=O.C=O>C(O)C>[NH2:8][C:9]1[C:14]([C:15]([NH2:17])=[O:16])=[C:13]([N:18]2[CH2:23][CH2:22][CH:21]([C:24]3[N:25]([CH2:40][CH:41]4[CH2:44][N:43]([CH3:2])[CH2:42]4)[CH:26]=[C:27]([C:29]4[CH:34]=[CH:33][C:32]([F:35])=[C:31]([C:36]([F:37])([F:39])[F:38])[CH:30]=4)[N:28]=3)[CH2:20][CH2:19]2)[N:12]=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 712FormaldehydeHCID 89442706HCID 89442706, compound

Product 1

HCID 89442639HCID 89442639, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 4-amino-6-{4-[1-azetidin-3-ylmethyl-4-(4-fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidine-5-carboxylic acid amide trifluoroacetate (2) (25.00 mg; 0.03 mmol; 1.00 eq.) in ethanol 1 ml added formic acid (0.00 1 ml; 0.08 mmol; 2.50 eq.) and formaldehyde (0.001 ml; 0.04 mmol; 1.20 eq.), stirred at 65° C. for 3 hr. lc-ms showed clean desired peak. Removed off solvent, purified by HPLC, collected title compound 14.8 mg. LC-MS (M+1=533, obsd.=533).

Workup

  1. customRemoved off solvent
  2. custompurified by HPLC
  3. customcollected title compound 14.8 mg

Sources & evidence

ORD record
ord-01c27987fa5a4f908bdc77f979fd8586
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

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