Hydrochloric Acid → HCID 69804566, compound

HRID 896359Notes

Reaction equation

HRID 896359 reaction equation
C(OC([NH:8][CH2:9][C:10]1[CH:47]=[CH:46][C:13]2[N:14]([CH2:35][CH2:36][CH2:37][CH2:38][O:39][C:40](=[O:45])[C:41]([CH3:44])([CH3:43])[CH3:42])[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:47]=[CH:46][C:13]2[N:14]([CH2:35][CH2:36][CH2:37][CH2:38][O:39][C:40](=[O:45])[C:41]([CH3:43])([CH3:44])[CH3:42])[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 69708345HCID 69708345, compound

Product 1

HCID 69804566HCID 69804566, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2,2-dimethyl-propionic 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 (59 mg, 0.089 mmol) and TFA (138 μL, 1.79 mmol) in dichloromethane (2 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 (233 μL, 10 equiv.) was added, followed by concentration. The residue was triturated from diethyl ether and filtered to give the title compound (46 mg, 87%) as a tan 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-9ffad9f54aca41d297b11c096af01ba3
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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