Hydrochloric Acid → HCID 20813988, compound

HRID 896379Notes

Reaction equation

HRID 896379 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:42]=[CH:41][C:12]2[N:13]([CH2:34][CH2:35][CH2:36][S:37]([CH3:40])(=[O:39])=[O: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.Cl>>[NH2:7][CH2:8][C:9]1[CH:42]=[CH:41][C:12]2[N:13]([CH2:34][CH2:35][CH2:36][S:37]([CH3:40])(=[O:38])=[O:39])[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:31])([F:30])[F:32])[C:18]3=[O:33])=[N:15][C:11]=2[CH:10]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 20814122HCID 20814122, compound

Product 1

HCID 20813988HCID 20813988, compoundYield 49.5%

Procedure

To a solution of [2-[2,4-dioxo-3-(2,2,2-trifluoro-ethyl)-3,4-dihydro-2H-quinazolin-1-ylmethyl]-1-(3-methanesulfonyl-propyl)-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester (40 mg, 0.064 mmol) was added HCl (5 ml, 4.0 M in dioxane) and the mixture stirred for 12 h. The solvent was removed to give a white solid. The solid was purified by preparative HPLC to give 16.6 mg (40%) of 1-[5-aminomethyl-1-(3-methanesulfonyl-propyl)-1H-benzoimidazol-2-ylmethyl]-3-(2,2,2-trifluoro-ethyl)-1H-quinazoline-2,4-dione as a white powder.

Workup

  1. customThe solvent was removed
  2. customto give a white solid
  3. customThe solid was purified by preparative HPLC

Sources & evidence

ORD record
ord-3ec76efa85f648808a15652ad32f6f0b
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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