HCID 118162075, compound → HCID 118162189, compound

HRID 1749485Notes

Reaction equation

[CH3:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH2:13][C:14]#[N:15])[CH:10]=[CH:11][CH:12]=2)[N:5]=[N:4][N:3]=1>C1COCC1>[CH3:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH2:13][CH2:14][NH2:15])[CH:10]=[CH:11][CH:12]=2)[N:5]=[N:4][N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 3-(5-methyl-tetrazol-1-yl)-phenyl-acetonitrile (180 mg, 0.90 mmol) in THF (3 mL) was added a solution of borane-methyl sulfide complex in THF (2M, 0.8 mL, 1.60 mmol) slowly at 0° C. and the resulting mixture was refluxed at 80° C. under nitrogen for 2 h. The reaction was quenched with MeOH and stirred at room temperature for 1 h. The mixture was concentrated to give the crude product, which was purified by silica gel column chromatography (10-26% ethyl acetate in petroleum ether) to afford the title compound (85 mg, 0.42 mmol, 46% yield). MS (ESI) m/z 204.1 [M+H]+.

Workup

customThe reaction was quenched with MeOH
concentrationThe mixture was concentrated
customto give the crude product, which
customwas purified by silica gel column chromatography (10-26% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-aedd7f931bfd4ad5a00008586c9988df
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156798B2

Reaction notes

Loading…