HCID 57973773, compound → HCID 11589768, compound

HRID 1863954Notes

Reaction equation

HRID 1863954 reaction equation
C(OC(=O)[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)(C)(C)C.[F:25][C:26]([F:38])([F:37])[C:27]1[N:36]=[C:30]2[C:31](=S)[NH:32][CH2:33][CH2:34][N:29]2[N:28]=1>COCCO>[F:23][C:16]1[CH:17]=[C:18]([F:22])[C:19]([F:21])=[CH:20][C:15]=1[CH2:14][C@@H:8]([NH2:7])[CH2:9][C:10]1[N:32]2[C:31]([C:30]3[N:29]([N:28]=[C:27]([C:26]([F:38])([F:37])[F:25])[N:36]=3)[CH2:34][CH2:33]2)=[N:13][N:12]=1

Participants

4

Reactant 2

HCID 57973773HCID 57973773, compound2×HCID 57973796HCID 57973796, compound2×

Product 1

HCID 11589768HCID 11589768, compound

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 208 mg (0.6 mmol) of of tert-butyl[(1R)-3-hydrazino-3-oxo-1-(2,4,5-trifluorobenzyl)propyl]carbamate (Intermediate 4), 100 mg (0.45 mmol) of 2-(trifluoromethyl)-6,7-dihydro[1,2,4]triazolo[1,5-a]pyrazine-8(5H)-thione (Intermediate 7), and 5 mL of 2-methoxyethanol was stirred at reflux for 18 h, resulting primarily in ring closure of the initial adduct as well as loss of the Boc group. The cooled solution was purified by preparative HPLC (C18 reverse phase column, 30-75% acetonitrile in water containing 0.05% trifluoroacetic acid) to afford the title compound.

Workup

  1. temperatureat reflux for 18 h

Sources & evidence

ORD record
ord-0478d6bd60f84a1caf4314db5c0fd9e2
Source dataset
uspto-grants-2009_12
Patent number
US07625888B2

Reaction notes

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