Ethanesulfonyl chloride → HCID 117777666, compound

HRID 64166Notes

Reaction equation

[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:9]=[C:10]([NH:29]C(=O)C)[CH:11]=[C:12]([N:14]2[C:18]3[CH:19]=[CH:20][C:21]([C:23]4[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=4)=[CH:22][C:17]=3[N:16]=[CH:15]2)[CH:13]=1.[CH2:33]([S:35](Cl)(=[O:37])=[O:36])[CH3:34]>>[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:9]=[C:10]([NH:29][S:35]([CH2:33][CH3:34])(=[O:37])=[O:36])[CH:11]=[C:12]([N:14]2[C:18]3[CH:19]=[CH:20][C:21]([C:23]4[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=4)=[CH:22][C:17]=3[N:16]=[CH:15]2)[CH:13]=1

Participants

Reactant 2

HCID 11667Ethanesulfonyl chloride

HCID 89501361N-(3-(3-fluoropyridin-4-yl)-5-(5-(1-methyl-1H-pyrazol-4-yl)-1H-benzo[d]-imidazol-1-yl)phenyl)acetamide

Product 1

HCID 117777666HCID 117777666, compoundYield 15.13%

Procedure

The compound was prepared from the compound of Example 277 (0.9 g, 2.11 mmol, 1 eq.) using the procedure of Example 2 and ethanesulfonyl chloride (60 mg, 0.46 mmol, 1.2 eq.) to give the product in 15.13% yield (28 mg). 1H NMR (400 MHz, DMSO-d6): δ 8.69-8.68 (d, 1H), 8.58 (s, 1H), 8.54-8.52 (d, 1H), 8.18 (s, 1H), 7.97 (s, 1H), 7.93 (s, 1H), 7.74-7.71 (t, 1H), 7.67-7.64 (d, 1H), 7.58-7.56 (d, 1H), 7.44-7.43 (t, 1H), 7.36-7.33 (d, 2H), 3.87 (s, 3H), 3.07-3.02 (quartet, 2H), 1.22-1.18 (t, 3H); LC-MS (ESI): Calculated mass: 476.14; Observed mass: 476.9 [M+H]+ (rt: 0.36 min).

Workup

customto give the product in 15.13% yield (28 mg)
custom476.9 [M+H]+ (rt: 0.36 min)

Sources & evidence

ORD record: ord-72945bd04af14f9fba57bdce91c3a554
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447091B2

Reaction notes

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