Acetyl chloride → HCID 20813989, compound

HRID 896362Notes

Reaction equation

HRID 896362 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:40]=[CH:39][C:12]2[N:13]([CH2:34][CH2:35][CH2:36][CH2:37][F:38])[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])[N:19]([CH2:28][C:29]([F:32])([F:31])[F:30])[C:18]3=[O:33])=[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:40]=[CH:39][C:12]2[N:13]([CH2:34][CH2:35][CH2:36][CH2:37][F:38])[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])[N:19]([CH2:28][C:29]([F:32])([F:31])[F:30])[C:18]3=[O:33])=[N:15][C:11]=2[CH:10]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6422Trifluoroacetic acidHCID 69719778HCID 69719778, compound

Product 1

HCID 20813989HCID 20813989, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of [2-[2,4-dioxo-3-(2,2,2-trifluoro-ethyl)-3,4-dihydro-2H-quinazolin-1-ylmethyl]-1-(4-fluoro-butyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester (51 mg, 0.088 mmol) in DCM (2 mL) was added TFA (204 μL, 2.65 mmol). The solution was allowed to reach room temperature and stirred for 6 hrs. The volatiles were removed in vacuo and the residue was stripped with methanol. The TFA salt was dissolved in methanol followed by the addition of acetyl cloride (63 μL, 0.88 mmol) and concentrated. This procedure was repeated once. The product was dissolve in methanol and DCM then concenrated (twice). The remaining solid was triturated in diethyl ether to give 1-[5-Aminomethyl-1-(4-fluoro-butyl)-1H-benzoimidazol-2-ylmethyl]-3-(2,2,2-trifluoro-ethyl)-1H-quinazoline-2,4-dione; HCl salt (45 mg, 100%) as a 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 dissolve in methanol
  6. customThe remaining solid was triturated in diethyl ether

Sources & evidence

ORD record
ord-dd838420a775457d881d004bc0949f6b
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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