Methanol → HCID 91477957, compound

HRID 1863953Notes

Reaction equation

HRID 1863953 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:11])([CH3:4])([CH3:3])[CH3:2].[F:25][C:26]([F:38])([F:37])[C:27]1[N:31]2[CH2:32][CH2:33][NH:34][C:35](=S)[C:30]2=[N:29][N:28]=1.CO>C(OCC)C>[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](=[O:11])[NH:12][NH:13][C:35]1[C:30]2[N:31]([C:27]([C:26]([F:38])([F:37])[F:25])=[N:28][N:29]=2)[CH2:32][CH2:33][N:34]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 57973784HCID 57973784, compound2×HCID 57973796HCID 57973796, compound2×

Product 1

HCID 91477957HCID 91477957, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 207 mg (0.6 mmol) of tert-butyl[(1R)-3-hydrazino-3-oxo-1-(2,4,5-trifluorobenzyl)propyl]carbamate (Intermediate 4), 110 mg (0.5 mmol) of 3-(trifluoromethyl)-6,7-dihydro[1,2,4]triazolo[4,3-a]pyrazine-8(5H)-thione (Intermediate 6), and 5.5 mL of methanol was stirred at reflux for 1 day. Diethyl ether was added to the cooled solution, resulting in precipitation. The solid was removed by filtration, and the filtrate was concentrated to dryness. Purification of the residue by preparative HPLC (C18 reverse phase column, 30-80% acetonitrile in water containing 0.05% trifluoroacetic acid) afforded the title compound. LC-MS 536 (M+1).

Workup

  1. temperatureat reflux for 1 day
  2. customresulting in precipitation
  3. customThe solid was removed by filtration
  4. concentrationthe filtrate was concentrated to dryness
  5. customPurification of the residue by preparative HPLC (C18 reverse phase column, 30-80% acetonitrile in water containing 0.05% trifluoroacetic acid)

Sources & evidence

ORD record
ord-7570d26c96434153b623cc6e9ec52412
Source dataset
uspto-grants-2009_12
Patent number
US07625888B2

Reaction notes

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