Acetic Anhydride → HCID 66868541, compound

HRID 250751Notes

Reaction equation

HRID 250751 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH:10]=[CH:11][C:12]3[N:16]=[C:15]([NH2:17])[N:14]([C@H:18]([CH3:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[C:13]=3[CH:24]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:32](OC(=O)C)(=[O:34])[CH3:33]>ClCCl>[C:1]1([C:7]#[C:8][C:9]2[CH:10]=[CH:11][C:12]3[N:16]=[C:15]([NH:17][C:32](=[O:34])[CH3:33])[N:14]([C@H:18]([CH3:23])[C:19]([CH3:20])([CH3:22])[CH3:21])[C:13]=3[CH:24]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 66868797HCID 66868797, compound

Product 1

HCID 66868541HCID 66868541, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add 6-phenylethynyl-1-(1-(R)-methyl-2,2-dimethylpropyl)-1H-benzimidazol-2-ylamine (5.81 g, 0.018 mol), triethylamine (12 mL), dichloromethane (100 mL), N,N-dimethylaminopyridine (0.11 g, 0.9 mmol), and acetic anhydride (7.5 mL) and stir for about 18 hours. Evaporate and redissolve in ethyl acetate and wash with water, 1N HCl (3×), saturated sodium bicarbonate, and saturated sodium chloride. Add 2M ammonia in methanol to organic layer and stir 10 minutes and evaporate. Redissolve in dichloromethane and wash with saturated sodium bicarbonate, saturated sodium chloride, dry magnesium sulfate, and concentrate to give the desired compound as an orange foam (6.92 g, quant).

Workup

  1. customEvaporate
  2. dissolutionredissolve in ethyl acetate
  3. washwash with water, 1N HCl (3×), saturated sodium bicarbonate, and saturated sodium chloride
  4. additionAdd 2M ammonia in methanol to organic layer
  5. stirringstir 10 minutes
  6. customevaporate
  7. dissolutionRedissolve in dichloromethane
  8. washwash with saturated sodium bicarbonate, saturated sodium chloride, dry magnesium sulfate
  9. concentrationconcentrate

Sources & evidence

ORD record
ord-b56b689f0f68405688f7cc0e4aac0d30
Source dataset
uspto-grants-2011_01
Patent number
US07863310B2

Reaction notes

Loading…