Acetyl chloride → HCID 20813993, compound

HRID 896358Notes

Reaction equation

HRID 896358 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][OH: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>ClCCl>[NH2:7][CH2:8][C:9]1[CH:40]=[CH:39][C:12]2[N:13]([CH2:34][CH2:35][CH2:36][CH2:37][OH: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 69719649HCID 69719649, compound

Product 1

HCID 20813993HCID 20813993, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of [2-[2,4-dioxo-3-(2,2,2-trifluoro-ethyl)-3,4-dihydro-2H-quinazolin-1-ylmethyl]-1-(4-hydroxy-butyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester (80 mg, 0.14 mmol) in dichloromethane (3 mL) was added TFA (319 μL, 4.14 mmol). The solution was allowed to stir for 6 hrs. followed by the removal of the volatiles in vacuo. The resulting trifluoroacetate was dissolved in methanol (3 mL) followed by the addition of acetyl cloride (98 μL, 1.4 mmol) and concentrated after 10 min. This procedure was repeated once allowing the reaction to run for 3 hrs. The solution was concentrated in vacuo and the residue stripped with DCM (thrice). The product was triturated in diethyl ether and the ether decanted to yield 1-[5-Aminomethyl-1-(4-hydroxy-butyl)-1H-benzoimidazol-2-ylmethyl]-3-(2,2,2-trifluoro-ethyl)-1H-quinazoline-2,4-dione; HCl salt (79 mg, 100%) as a white solid:

Workup

  1. customfollowed by the removal of the volatiles in vacuo
  2. dissolutionThe resulting trifluoroacetate was dissolved in methanol (3 mL)
  3. concentrationconcentrated after 10 min
  4. customthe reaction
  5. waitto run for 3 hrs
  6. concentrationThe solution was concentrated in vacuo
  7. customThe product was triturated in diethyl ether
  8. customthe ether decanted

Sources & evidence

ORD record
ord-80656de0bb944c5aab30b3a546253ab8
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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