Trifluoroacetic acid → HCID 66980615, compound

HRID 1038820Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([CH2:17][NH:18]CC3C=CC(OC)=CC=3OC)=[N:15][CH:16]=[C:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:30]([OH:36])([C:32]([F:35])([F:34])[F:33])=[O:31].C([SiH](CC)CC)C>C(Cl)Cl>[F:33][C:32]([F:35])([F:34])[C:30]([OH:36])=[O:31].[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([CH2:17][NH2:18])=[N:15][CH:16]=[C:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 55 °C

Procedure

A flask was charged with 1-(7-benzyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazin-3-yl)-N-(2,4-dimethoxybenzyl)methanamine (1.0 g, 2.6 mmol, prepared using H from 7-benzyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine-3-carbaldehyde [WO 03/076427, Preparation 138] with 2,4-dimethoxybenzylamine), DCM (20 mL) and TFA (10 mL). To the mixture was added triethylsilane (0.50 mL, 3.1 mmol) and the mixture was heated to about 55° C. for about 6 h. The solvents were removed under reduced pressure to give (7-benzyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazin-3-yl)methanamine 2,2,2-trifluoroacetate (1.6 g) as a crude material that was used directly without further purification: LC/MS (Table 2, Method h) Rt=1.65 min; MS m/z: 243 (M+H)+.

Workup

customThe solvents were removed under reduced pressure

Sources & evidence

ORD record: ord-a0158801283b4b54bf6974fc282fbcae
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08551981B2

Reaction notes

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