Bromoacetonitrile → HCID 86615242, compound

HRID 2244390Notes

Reaction equation

[NH2:1][C:2]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:3]=1[C:4]([N:6]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:22][CH:21]=1)[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1)=[O:5].Br[CH2:36][C:37]#[N:38].[Na].[H][H]>C(O)C>[C:26]([C:23]1[CH:24]=[CH:25][C:20]([CH2:19][N:6]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:16])([F:17])[F:18])[CH:10]=2)[C:4](=[O:5])[C:3]2[CH:30]=[C:31]([Cl:34])[CH:32]=[CH:33][C:2]=2[NH:1][CH2:36][C:37]#[N:38])=[CH:21][CH:22]=1)([CH3:29])([CH3:28])[CH3:27]

Participants

Conditions

Temperature: 100 °C

Procedure

2-Amino-N-(4-tert-butyl-benzyl)-5-chloro-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamide (80 mg, 0.164 mmol), bromo-acetonitrile (21 mg, 0.172 mmol) and sodium hydrogen catbonat (17 mg, 01.96 mmol) were suspended in ethanol (21 ml) and heated to 100° C. for 3 days. The reaction mixture was cooled to RT, filtered and the precipitate was washed with ethanol. The solvent of the filtrate was concentrated in vacuo to give a residue which was purified by flash column chromatography (heptane/ethyl acetate 7:3) to yield the desired product (26 mg, 30%) as a yellow solid. MS (ISP) 526.2 (M−H)−.

Workup

temperatureThe reaction mixture was cooled to RT
filtrationfiltered
washthe precipitate was washed with ethanol
concentrationThe solvent of the filtrate was concentrated in vacuo
customto give a residue which
customwas purified by flash column chromatography (heptane/ethyl acetate 7:3)

Sources & evidence

ORD record: ord-78c79acb5d0544c0a040919c926298de
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07678818B2

Reaction notes

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