HCID 117777631, compound → HCID 117777624, compound

HRID 64170Notes

Reaction equation

HRID 64170 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][C:39](=[O:41])[CH3:40])[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][C:39](=[O:41])[CH3:40])[CH:27]=1

Participants

3

Reactant 1

HCID 117777631HCID 117777631, compound

Product 1

HCID 117777624HCID 117777624, compoundYield 84.3%

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)acetamide (0.10 g, 0.182 mmol) in TFA (4 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 84.3% yield (0.70 g)1H NMR (400 MHz, DMSO-d6): δ 10.42 (s, 1H), 8.98 (s, 1H), 8.68-8.67 (D, 1H), 8.43 (d, 1H), 8.31 (s, 1H), 7.99-7.96 (dd, 1H), 7.89 (s, 2H), 7.76-7.70 (m, 2H), 7.49-7.43 (m, 1H), 7.31-7.26 (m, 1H), 6.51-6.48 (d, 1H), 2.13 (s, 3H); LC-MS (ESI): Calculated mass 457.43: Observed mass: 458.1[M+H]+ (rt: 0.68 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 84.3% yield (0.70 g)1H NMR (400 MHz, DMSO-d6): δ 10.42 (s, 1H), 8.98 (s, 1H), 8.68-8.67 (D, 1H), 8.43 (d, 1H), 8.31 (s, 1H), 7.99-7.96 (dd, 1H), 7.89 (s, 2H), 7.76-7.70 (m, 2H), 7.49-7.43 (m, 1H), 7.31-7.26 (m, 1H), 6.51-6.48 (d, 1H), 2.13 (s, 3H)
  6. custom458.1[M+H]+ (rt: 0.68 min)

Sources & evidence

ORD record
ord-63909f1c2f7c4ef0a59e8e617909a57d
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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