Cyclopropanesulfonyl chloride → N-(5-(6-(1-cyclopentyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-3-yl)-2',4'-difluoro-[1,1'-biphenyl]-3-yl)cyclopropanesulfonamide

HRID 64187Notes

Reaction equation

HRID 64187 reaction equation
Br[C:2]1[CH:3]=[C:4]2[N:10]=[CH:9][N:8]([C:11]3[CH:12]=[C:13]([NH2:25])[CH:14]=[C:15]([C:17]4[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=4[F:24])[CH:16]=3)[C:5]2=[N:6][CH:7]=1.[CH:26]1([S:29](Cl)(=[O:31])=[O:30])[CH2:28][CH2:27]1.[CH:33]1([N:38]2[CH:42]=[C:41](B3OC(C)(C)C(C)(C)O3)[CH:40]=[N:39]2)[CH2:37][CH2:36][CH2:35][CH2:34]1>>[CH:33]1([N:38]2[CH:42]=[C:41]([C:2]3[CH:3]=[C:4]4[N:10]=[CH:9][N:8]([C:11]5[CH:12]=[C:13]([NH:25][S:29]([CH:26]6[CH2:28][CH2:27]6)(=[O:31])=[O:30])[CH:14]=[C:15]([C:17]6[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=6[F:24])[CH:16]=5)[C:5]4=[N:6][CH:7]=3)[CH:40]=[N:39]2)[CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

4

Reactant 3

HCID 2760919Cyclopropanesulfonyl chlorideHCID 567767301-Cyclopentyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 89500107HCID 89500107, compound

Product 1

HCID 89501513N-(5-(6-(1-cyclopentyl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridin-3-yl)-2',4'-difluoro-[1,1'-biphenyl]-3-yl)cyclopropanesulfonamideYield 27.86%

Procedure

The compound was prepared using the procedures of Example 334 starting from 5-(6-bromo-3H-imidazo[4,5-b]pyridin-3-yl)-2′,4′-difluoro-[1,1′-biphenyl]-3-amine (133 mg, 0.33 mmol) and using cyclopropanesulfonyl chloride (20 mg, 0.66 mmol, 2.0 eq.) and 1-cyclopentyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.115 g, 0.43 mmol, 2.0 eq.) to give the crude residue which was purified by preparative HPLC to give the product in 27.86% yield (34 mg). 1H NMR (400 MHz, DMSO-d6): δ 10.26 (s, 1H), 8.96 (s, 1H), 8.76-8.75 (d, 1H), 8.45-8.42 (t, 2H), 8.06 (s, 1H), 8.00-7.99 (d, 1H), 7.78-7.70 (m, 2H), 7.49-7.43 (m, 2H), 7.31-7.26 (t, 1H), 4.74-4.70 (t, 1H), 2.84 (m, 1H), 2.14-2.08 (m, 2H), 2.00-1.96 (m, 2H), 1.84-1.81 (m, 2H), 1.69-1.65 (m, 2H), 1.09-1.02 (m, 4H); LC-MS (ESI): Calculated mass: 560.18; Observed mass: 561.2 [M+H]+ (rt: 1.70 min).

Workup

  1. customThe compound was prepared

Sources & evidence

ORD record
ord-b6f8e47d317e4d86b01989f1bce523e1
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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