Thiourea → HCID 117777552, compound

HRID 64154Notes

Reaction equation

Br[CH2:2][C:3]([C:5]1[CH:31]=[CH:30][C:8]2[N:9]([C:12]3[CH:13]=[C:14]([NH:26][C:27](=[O:29])[CH3:28])[CH:15]=[C:16]([C:18]4[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=4[F:25])[CH:17]=3)[CH:10]=[N:11][C:7]=2[CH:6]=1)=O.[NH2:32][C:33]([NH2:35])=[S:34]>C(O)C>[NH2:35][C:33]1[S:34][C:3]([C:5]2[CH:31]=[CH:30][C:8]3[N:9]([C:12]4[CH:13]=[C:14]([NH:26][C:27](=[O:29])[CH3:28])[CH:15]=[C:16]([C:18]5[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=5[F:25])[CH:17]=4)[CH:10]=[N:11][C:7]=3[CH:6]=2)=[CH:2][N:32]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of N-(5-(5-(2-bromoacetyl)-1H-benzo[d]imidazol-1-yl)-2′,4′-difluoro-[1,1′-biphenyl]-3-yl)acetamide (100 mg, 0.20 mmol) in ethanol was added thiourea (20 mg, 0.30 mmol, 1.5 eq). The mixture was stirred at 60° C. for 3 h. The mixture was quenched and extracted as in Example 1(d). The solvent was distilled off to give the crude residue which was purified by preparative HPLC to give the product in 14.7% yield (14 mg). 1H NMR (300 MHz, CD3OD): δ 8.73 (s, 1H), 8.11 (s, 1H), 8.01 (s, 1H), 7.73-7.69 (m, 2H), 7.62-7.50 (m, 2H), 7.45 (d, 1H), 7.10-6.99 (m, 3H), 2.10 (s, 3H); LC-MS (ESI): Calculated mass: 461.4; Observed mass: 462.1 [M+H]+ (rt: 0.80 min).

Workup

customThe mixture was quenched
extractionextracted as in Example 1(d)
distillationThe solvent was distilled off

Sources & evidence

ORD record: ord-139f855e69c94e98adac2926e277258c
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447091B2

Reaction notes

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