Hydrochloric Acid → HCID 69753219, compound

HRID 896360Notes

Reaction equation

HRID 896360 reaction equation
C(OC([NH:8][CH2:9][C:10]1[CH:44]=[CH:43][C:13]2[N:14]([CH2:35][CH2:36][CH2:37][CH2:38][O:39][C:40](=[O:42])[CH3:41])[C:15]([CH2:17][N:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[C:21](=[O:28])[N:20]([CH2:29][C:30]([F:33])([F:32])[F:31])[C:19]3=[O:34])=[N:16][C:12]=2[CH:11]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.Cl.O1CCOCC1>ClCCl>[NH2:8][CH2:9][C:10]1[CH:44]=[CH:43][C:13]2[N:14]([CH2:35][CH2:36][CH2:37][CH2:38][O:39][C:40](=[O:42])[CH3:41])[C:15]([CH2:17][N:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[C:21](=[O:28])[N:20]([CH2:29][C:30]([F:33])([F:31])[F:32])[C:19]3=[O:34])=[N:16][C:12]=2[CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 312751,4-DioxaneHCID 69708703HCID 69708703, compound

Product 1

HCID 69753219HCID 69753219, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of acetic acid 4-{5-(tert-butoxycarbonylamino-methyl)-2-[2,4-dioxo-3-(2,2,2-trifluoro-ethyl)-3,4-dihydro-2H-quinazolin-1-ylmethyl]-benzoimidazol-1-yl}-butyl ester (98 mg, 0.16 mmol) and TFA (244 μL, 3.17 mmol) in dichloromethane (3 mL) was stirred for 4 hrs at room temperature. The volatiles were removed in vacuo and the residue dissolved in dichloromethane. A solution of 4N HCl in dioxane (0.4 mL, 10 equiv.) was added, followed by concentration. The residue was triturated from diethyl ether and filtered to give acetic acid 4-{5-aminomethyl-2-[2,4-dioxo-3-(2,2,2-trifluoro-ethyl)-3,4-dihydro-2H-quinazolin-1-ylmethyl]-benzoimidazol-1-yl }-butyl ester; HCl salt (53 mg, 60%) as a white solid:

Workup

  1. customThe volatiles were removed in vacuo
  2. dissolutionthe residue dissolved in dichloromethane
  3. concentrationfollowed by concentration
  4. customThe residue was triturated from diethyl ether
  5. filtrationfiltered

Sources & evidence

ORD record
ord-ff0fed5364b34aa7b41fcd55fda87c06
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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