HCID 117777756, compound → N-(2',4'-difluoro-5-(6-(6-oxo-1,6-dihydropyridin-3-yl)-3H-imidazo[4,5-b]-pyridin-3-yl)-[1,1'-biphenyl]-3-yl)ethanesulfonamide

HRID 64171Notes

Reaction equation

HRID 64171 reaction equation
C([O:8][C:9]1[N:14]=[CH:13][C:12]([C:15]2[CH:16]=[C:17]3[N:23]=[CH:22][N:21]([C:24]4[CH:25]=[C:26]([NH:38][S:39]([CH2:42][CH3:43])(=[O:41])=[O:40])[CH:27]=[C:28]([C:30]5[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=5[F:37])[CH:29]=4)[C:18]3=[N:19][CH:20]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>C(O)(C(F)(F)F)=O>[F:37][C:31]1[CH:32]=[C:33]([F:36])[CH:34]=[CH:35][C:30]=1[C:28]1[CH:29]=[C:24]([N:21]2[C:18]3=[N:19][CH:20]=[C:15]([C:12]4[CH:11]=[CH:10][C:9](=[O:8])[NH:14][CH:13]=4)[CH:16]=[C:17]3[N:23]=[CH:22]2)[CH:25]=[C:26]([NH:38][S:39]([CH2:42][CH3:43])(=[O:41])=[O:40])[CH:27]=1

Participants

3

Reactant 1

HCID 117777756HCID 117777756, compound

Product 1

HCID 89501155N-(2',4'-difluoro-5-(6-(6-oxo-1,6-dihydropyridin-3-yl)-3H-imidazo[4,5-b]-pyridin-3-yl)-[1,1'-biphenyl]-3-yl)ethanesulfonamideYield 23.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of N-(5-(6-(6-(benzyloxy)pyridin-3-yl)-3H-imidazo[4,5-b]pyridin-3-yl)-2′,4′-difluoro-[1,1′-biphenyl]-3-yl)ethanesulfonamide (0.140 g, 0.234 mmol) in TFA (5 ml) was stirred at RT for 16 h. The mixture was concentrated on vacuo, quenched with sodium bicarbonate and extracted as in Example 1(d). The solvent was distilled off to give the product in 23.7% yield (0.028 g). 1H NMR (400 MHz, DMSO-d6): δ 10.35 (s, 1H), 9.07 (s, 1H), 8.70 (s, 1H), 8.44 (s, 1H), 8.01 (d, 1H), 7.93 (s, 2H), 7.78-7.72 (m, 2H), 7.48-7.45 (d, 2H), 7.30-7.26 (t, 1H), 6.52-6.50 (d, 1H), 3.30-3.28 (q, 2H), 1.28-1.25 (t, 3H); LC-MS (ESI): Calculated mass: 507.51; Observed mass: 508.1 [M+H]+ (rt: 0.1 min).

Workup

  1. concentrationThe mixture was concentrated on vacuo
  2. customquenched with sodium bicarbonate
  3. extractionextracted as in Example 1(d)
  4. distillationThe solvent was distilled off
  5. customto give the product in 23.7% yield (0.028 g)
  6. custom508.1 [M+H]+ (rt: 0.1 min)

Sources & evidence

ORD record
ord-a3fb0f4c90174062af96360453728b78
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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