Acetyl chloride → HCID 44433608, compound

HRID 896366Notes

Reaction equation

HRID 896366 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:36]=[CH:35][C:12]2[N:13]([CH2:30][CH2:31][CH2:32][CH2:33][F:34])[C:14]([CH2:16][N:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]([O:27][CH3:28])=[CH:19][C:18]3=[O:29])=[N:15][C:11]=2[CH:10]=1)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)(=O)C>C(Cl)Cl>[NH2:7][CH2:8][C:9]1[CH:36]=[CH:35][C:12]2[N:13]([CH2:30][CH2:31][CH2:32][CH2:33][F:34])[C:14]([CH2:16][N:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]([O:27][CH3:28])=[CH:19][C:18]3=[O:29])=[N:15][C:11]=2[CH:10]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6422Trifluoroacetic acidHCID 69718179HCID 69718179, compound

Product 1

HCID 44433608HCID 44433608, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of [1-(4-fluoro-butyl)-2-(4-methoxy-2-oxo-2H-quinolin-1-ylmethyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester (20 mg, 0.039 mmol) in DCM (1 mL) was added TFA (91 μL, 1.2 mmol). The solution was allowed to reach room temperature and stirred for 3 hrs. The volatiles were removed in vacuo and the residue was stripped with DCM and methanol. The TFA salt was dissolved in methanol followed by the addition of acetyl cloride (28 μL, 0.39 mmol) and concentrated. The product was dissolved in methanol and dichloromethane and concentrated (twice) then the resiude was triturated in diethyl ether to give 1-[5-aminomethyl-1-(4-fluoro-butyl)-1H-benzoimidazol-2-ylmethyl]-4-methoxy-1H-quinolin-2-one; HCl salt (11 mg, 65%) as an off white solid:

Workup

  1. customto reach room temperature
  2. customThe volatiles were removed in vacuo
  3. dissolutionThe TFA salt was dissolved in methanol
  4. concentrationconcentrated
  5. dissolutionThe product was dissolved in methanol
  6. concentrationdichloromethane and concentrated (twice) then the resiude
  7. customwas triturated in diethyl ether

Sources & evidence

ORD record
ord-42c22f5915c746428a01fa944d0fe229
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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