Benzyl chloromethyl ether → 7-N-(tert-Butoxycarbonyl)-8-[(benzyloxy)methyl]-2-(trifluoromethyl)-5,6,7,8 tetrahydro[1,2,4]triazolo[1,5-alpha]pyrazine

HRID 133076Notes

Reaction equation

HRID 133076 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[N:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[N:16]=[C:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[CH2:22][O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[N:14]=[C:15]([C:17]([F:18])([F:19])[F:20])[N:16]=[C:10]2[CH:9]1[CH2:22][O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 137983Benzyl chloromethyl etherHCID 53393358tert-Butyl 2-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[1,5-a]pyrazine-7(8H)-carboxylate

Product 1

HCID 693624067-N-(tert-Butoxycarbonyl)-8-[(benzyloxy)methyl]-2-(trifluoromethyl)-5,6,7,8 tetrahydro[1,2,4]triazolo[1,5-alpha]pyrazine

Procedure

The title compound was prepared from 2.06 g (7.06 mmol) of 7-N-(tert-butoxycarbonyl)-2-(trifluoromethyl)-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-α]pyrazine (Example 2, Step A) and benzyl chloromethyl ether essentially following the procedure outlined in Example 2, Step B. Purification by flash chromatography (silica gel, 5 to 10% ethyl acetate/hexane gradient) gave the title compound as a white foam. LC/MS 357 (M+1-tBu).

Workup

  1. customPurification by flash chromatography (silica gel, 5 to 10% ethyl acetate/hexane gradient)

Sources & evidence

ORD record
ord-6b60715354c14ccb8631fab76761d95e
Source dataset
uspto-grants-2008_06
Patent number
US07390809B2

Reaction notes

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