HCID 57973779, compound → HCID 91433405, compound

HRID 1863960Notes

Reaction equation

HRID 1863960 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][C@H:8]([CH2:14][C:15]1[CH:20]=[C:19]([F:21])[C:18]([F:22])=[CH:17][C:16]=1[F:23])[CH2:9][C:10]([NH:12][NH2:13])=O)([CH3:4])([CH3:3])[CH3:2].[F:25][C:26]([F:38])([F:37])[C:27]1[N:28]=[C:29]2[C:34](=S)[NH:33][CH2:32][CH2:31][N:30]2[CH:36]=1>COCCO>[C:1]([O:5][C:6](=[O:24])[NH:7][C@H:8]([CH2:14][C:15]1[CH:20]=[C:19]([F:21])[C:18]([F:22])=[CH:17][C:16]=1[F:23])[CH2:9][C:10]1[N:33]2[C:34]([C:29]3[N:30]([CH:36]=[C:27]([C:26]([F:38])([F:25])[F:37])[N:28]=3)[CH2:31][CH2:32]2)=[N:13][N:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 57973779HCID 57973779, compound2×HCID 57973796HCID 57973796, compound2×

Product 1

HCID 91433405HCID 91433405, compound

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 129 mg (0.475 mmol) of tert-butyl[(1R)-3-hydrazino-3-oxo-1-(2,4,5-trifluorobenzyl)propyl]carbamate (Intermediate 4), 129 mg (0.583 mmol) of 2-(trifluoromethyl)-6,7-dihydroimidazo[1,2-a]pyrazine-8(5H)-thione (Intermediate 11), and 8.5 mL of 2-methoxyethanol was stirred at reflux for 3 days. The cooled solution was concentrated, and the residue was purified by preparative HPLC (C18 reverse phase column, 20-90% acetonitrile in water containing 0.05% trifluoroacetic acid) to give the title compound as an oil. LC-MS 517 (M+1).

Workup

  1. temperatureat reflux for 3 days
  2. concentrationThe cooled solution was concentrated
  3. customthe residue was purified by preparative HPLC (C18 reverse phase column, 20-90% acetonitrile in water containing 0.05% trifluoroacetic acid)

Sources & evidence

ORD record
ord-12ddbffb4d174b8f80d2bc8dcc7007d8
Source dataset
uspto-grants-2009_12
Patent number
US07625888B2

Reaction notes

Loading…