Acetyl chloride → N-(2',4'-difluoro-5-(5-(1-(2-hydroxyethyl)-1H-pyrazol-4-yl)-1H-benzo[d]-imidazol-1-yl)-[1,1'-biphenyl]-3-yl) methane sulfonamide

HRID 64184Notes

Reaction equation

HRID 64184 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[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]([CH2:29][CH2:30][O:31]C5CCCCO5)[CH:28]=4)=[CH:23][C:18]=3[N:17]=[CH:16]2)[CH:12]=[C:11]([NH:38][S:39]([CH3:42])(=[O:41])=[O:40])[CH:10]=1.C(Cl)(=O)C>CO>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[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]([CH2:29][CH2:30][OH:31])[CH:28]=4)=[CH:23][C:18]=3[N:17]=[CH:16]2)[CH:12]=[C:11]([NH:38][S:39]([CH3:42])(=[O:41])=[O:40])[CH:10]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 117777730HCID 117777730, compound

Product 1

HCID 89501225N-(2',4'-difluoro-5-(5-(1-(2-hydroxyethyl)-1H-pyrazol-4-yl)-1H-benzo[d]-imidazol-1-yl)-[1,1'-biphenyl]-3-yl) methane sulfonamideYield 49.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(2′,4′-difluoro-5-(5-(1-(2-((tetrahydro-2H-pyran-2-yl)oxy)-ethyl)-1H-pyrazol-4-yl)-1H-benzo[d]imidazol-1-yl)-[1,1′-biphenyl]-3-yl)methanesulfonamide (0.15 g, 0.252 mmol) in methanol (5 ml) was added acetyl chloride (1 ml) at 0° C. as in Example 1(d). The solvent was distilled off to afford the product (0.063 g). 1H NMR (300 MHz, DMSO-d6): δ 8.64 (s, 1H), 8.22 (s, 1H), 8.00-7.97 (d, 2H), 7.80-7.69 (m, 2H), 7.67-7.61 (m, 1H), 7.59-7.60 (d, 1H), 7.53 (s, 2H), 7.47-7.41 (m, 2H), 7.29-7.25 (t, 1H), 4.97-4.95 (t, 1H), 4.18-4.15 (m, 2H), 3.80-3.78 (m, 2H), 3.14 (s, 3H) Calculated mass: 509.1; Observed mass: 510.3 [M+H]+ (rt: 1.18 min).

Workup

  1. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-368dccef5bd64eee93ce9e2d78a2182d
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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