Acetyl chloride → HCID 117777388, compound

HRID 64182Notes

Reaction equation

HRID 64182 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[C:13]([N:15]2[C:19]3[CH:20]=[CH:21][C:22]([C:24]4[CH:25]=[N:26][N:27]([CH2:29][CH2:30][O:31]C5CCCCO5)[CH:28]=4)=[CH:23][C:18]=3[N:17]=[CH:16]2)[CH:12]=[C:11]([NH:38]C(=O)C)[CH:10]=1.C(Cl)(=O)C>CO>[NH2:38][C:11]1[CH:12]=[C:13]([N:15]2[C:19]3[CH:20]=[CH:21][C:22]([C:24]4[CH:25]=[N:26][N:27]([CH2:29][CH2:30][OH:31])[CH:28]=4)=[CH:23][C:18]=3[N:17]=[CH:16]2)[CH:14]=[C:9]([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])[CH:10]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 117777820N-(2',4'-difluoro-5-(5-(1-(2-((tetrahydro-2H-pyran-2-yl)oxy)-ethyl)-1H-pyrazol-4-yl)-1H-benzo[d]imidazol-1-yl)-[1,1'-biphenyl]-3-yl)acetamide

Product 1

HCID 117777388HCID 117777388, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(2′,4′-difluoro-5-(5-(1-(2-((tetrahydro-2H-pyran-2-yl)oxy)-ethyl)-1H-pyrazol-4-yl)-1H-benzo[d]imidazol-1-yl)-[1,1′-biphenyl]-3-yl)acetamide (0.12 g, 0.125 mmol) in methanol (5 ml) was added (1 ml) acetyl chloride at 0° C. The mixture was stirred at RT for 16 h. The mixture was quenched and extracted as in Example 1(d). The solvent was distilled off to afford the product in 28% yield (0.026 g). 1H NMR (400 MHz, DMSO-d6): δ 8.53 (s, 1H), 8.20 (s, 1H), 7.97-7.95 (d, 2H), 7.69-7.64 (m, 2H), 7.59-7.56 (dd, 1H), 7.39-7.36 (m, 1H), 6.88 (s, 2H), 6.82 (d, 1H), 5.70 (s, 2H), 4.95 (s, 1H), 4.19-4.16 (t, 2H), 3.81-3.78 (t, 2H); LC-MS (ESI): Calculated mass: 431.44; Observed mass: 432.2 [M+H]+ (rt: 0.4 min).

Workup

  1. customThe mixture was quenched
  2. extractionextracted as in Example 1(d)
  3. distillationThe solvent was distilled off
  4. customto afford the product in 28% yield (0.026 g)
  5. custom432.2 [M+H]+ (rt: 0.4 min)

Sources & evidence

ORD record
ord-d54d4d13527e4b5a9f37d7bee67eafca
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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