Hydrochloric Acid → 2-(3-Cyclopropyl-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-5-carboxylic acid methyl ester

HRID 896373Notes

Reaction equation

HRID 896373 reaction equation
C(OC(=O)NC[C:9]1[CH:38]=[CH:37][C:12]2[N:13]([CH2:32][CH2:33][CH:34]([CH3:36])[CH3:35])[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]([CH:28]4[CH2:30][CH2:29]4)[C:18]3=[O:31])=[N:15][C:11]=2[CH:10]=1)(C)(C)C.C1(N2C(=O)C3C(=CC=CC=3)NC2=O)CC1.[CH3:55][O:56][C:57](C1C=CC2N(CCC(C)C)C(CCl)=NC=2C=1)=[O:58].Cl>O>[CH3:55][O:56][C:57]([C:9]1[CH:38]=[CH:37][C:12]2[N:13]([CH2:32][CH2:33][CH:34]([CH3:36])[CH3:35])[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]([CH:28]4[CH2:29][CH2:30]4)[C:18]3=[O:31])=[N:15][C:11]=2[CH:10]=1)=[O:58]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 172214493-cyclopropyl-1H-quinazoline-2,4-dioneHCID 697093472-chloromethyl-1-(3-methyl-butyl)-1H-benzoimidazole-5-carboxylic acid methyl esterHCID 69718855[2-(3-cyclopropyl-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester

Product 1

HCID 444336162-(3-Cyclopropyl-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-5-carboxylic acid methyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The procedure for the preparation of [2-(3-cyclopropyl-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester was followed starting from 3-cyclopropyl-1H-quinazoline-2,4-dione (309 mg, 1.53 mmol) and 2-chloromethyl-1-(3-methyl-butyl)-1H-benzoimidazole-5-carboxylic acid methyl ester; HCl salt (506 mg, 1.53 mmol). At the end of the reaction a precipitate had formed. The mixture was diluted with water, and the solid collected by filtration. After washing with water and diethyl ether and drying in vacuo, 2-(3-Cyclopropyl-2,4-dioxo-3,4-dihydro-2H-quinazolin-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-5-carboxylic acid methyl ester (634 mg, 90%) was obtained as a white solid:

Workup

  1. customAt the end of the reaction a precipitate
  2. customhad formed
  3. filtrationthe solid collected by filtration
  4. washAfter washing with water and diethyl ether
  5. customdrying in vacuo

Sources & evidence

ORD record
ord-291be803281f45fa984327f24168a116
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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