Ethanesulfonyl chloride → N-(2',5'-difluoro-5-(5-(1-methyl-1H-pyrazol-4-yl)-1H-benzo[d]imidazol-1-yl)-[1,1'-biphenyl]-3-yl)ethanesulfonamide

HRID 64188Notes

Reaction equation

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

Participants

Reactant 2

HCID 11667Ethanesulfonyl chloride

HCID 117777887HCID 117777887, compound

Product 1

HCID 89501164N-(2',5'-difluoro-5-(5-(1-methyl-1H-pyrazol-4-yl)-1H-benzo[d]imidazol-1-yl)-[1,1'-biphenyl]-3-yl)ethanesulfonamideYield 16.2%

Procedure

The compound was prepared from 2′,5′-difluoro-5-(5-(1-methyl-1H-pyrazol-4-yl)-1H-benzo[d]imidazol-1-yl)-[1,1′-biphenyl]-3-amine (70 mg, 0.175 mmol) using the procedure of Example 2(b) and ethanesulfonyl chloride (26 mg, 0.21 mmol, 1.2 eq.) to give the pure product in 16.2% yield (14 mg). NMR (400 MHz, DMSO-D6): δ10.35 (s, 1H), 8.80 (s, 1H), 8.23 (s, 1H), 8.00 (s, 1H), 7.96 (s, 1H), 7.70 (d, 1H), 7.65-7.60 (m, 4H), 7.51 (s, 2H), 7.49-7.39 (m, 1H), 3.88 (s, 3H), 3.30 (q, 2H), 1.26 (t, 3H), LC-MS (ESI): Calculated mass: 493.53; Observed mass: 494.2 [M+H]+ (rt: 0.1.33 min).

Workup

customto give the pure product in 16.2% yield (14 mg)
custom494.2 [M+H]+ (rt: 0.1.33 min)

Sources & evidence

ORD record: ord-7c14912a7be747e19b8a6a59011adc20
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447091B2

Reaction notes

Loading…