Ethanesulfonyl chloride → HCID 117778003, compound

HRID 64169Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([N:16]2[C:20]3[CH:21]=[CH:22][C:23]([C:25]4[CH:26]=[N:27][N:28]([CH2:30][CH2:31][C:32]([CH3:35])([OH:34])[CH3:33])[CH:29]=4)=[CH:24][C:19]=3[N:18]=[CH:17]2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=2[F:15])[CH:7]=1.[CH2:36]([S:38](Cl)(=[O:40])=[O:39])[CH3:37]>>[F:15][C:9]1[CH:10]=[C:11]([F:14])[CH:12]=[CH:13][C:8]=1[C:6]1[CH:5]=[C:4]([N:16]2[C:20]3[CH:21]=[CH:22][C:23]([C:25]4[CH:26]=[N:27][N:28]([CH2:30][CH2:31][C:32]([OH:34])([CH3:35])[CH3:33])[CH:29]=4)=[CH:24][C:19]=3[N:18]=[CH:17]2)[CH:3]=[C:2]([NH:1][S:38]([CH2:36][CH3:37])(=[O:40])=[O:39])[CH:7]=1

Participants

Reactant 2

HCID 11667Ethanesulfonyl chloride

HCID 117777863HCID 117777863, compound

Product 1

HCID 117778003HCID 117778003, compoundYield 33.6%

Procedure

The compound was prepared from 4-(4-(1-(5-amino-2′,4′-difluoro-[1,1′-biphenyl]-3-yl)-1H-benzo[d]imidazol-5-yl)-1H-pyrazol-1-yl)-2-methylbutan-2-ol (88 mg, 0.185 mmol) using the procedure of Example 2(b) and ethanesulfonyl chloride (28.6 mg, 0.370 mmol, 1.2 eq.) to give the product in 33.6% yield (35 mg)1H NMR (300 MHz, DMSO-d6): δ 10.42 (s, 1H), 8.92 (s, 1H), 8.30 (s, 1H), 8.01-7.97 (d, 2H), 7.69 (m, 3H), 7.59 (d, 2H), 7.56 (m, 2H), 7.32 (m, 1H), 4.30 (m, 2H), 3.31-3.28 (m, 4H), 1.8 (m, 2H), 1.28-1.24 (t, 3H), 1.15 (s, 6H), Calculated mass: 565.63; Observed mass: 566.2 [M+H]+ (rt: 1.40 min).

Workup

customto give the product in 33.6% yield (35 mg)1H NMR (300 MHz, DMSO-d6): δ 10.42 (s, 1H), 8.92 (s, 1H), 8.30 (s, 1H), 8.01-7.97 (d, 2H), 7.69 (m, 3H), 7.59 (d, 2H), 7.56 (m, 2H), 7.32 (m, 1H), 4.30 (m, 2H), 3.31-3.28 (m, 4H), 1.8 (m, 2H), 1.28-1.24 (t, 3H), 1.15 (s, 6H), Calculated mass
custom566.2 [M+H]+ (rt: 1.40 min)

Sources & evidence

ORD record: ord-6a382135ec6d4adea45d9176f9a1ea86
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447091B2

Reaction notes

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