Methanol → HCID 178479978, compound

HRID 1012155Notes

Reaction equation

HRID 1012155 reaction equation
C(OC(=O)[NH:7][CH:8]([C:15](=[O:38])[NH:16][C:17]1[C:18]([C:22]2[N:26]([CH3:27])[C:25]3[CH:28]=[CH:29][C:30]([N:32]4[CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)=[CH:31][C:24]=3[N:23]=2)=[N:19][NH:20][CH:21]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(C)(C)C.CO>Cl.O1CCOCC1>[NH2:7][CH:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:15]([NH:16][C:17]1[C:18]([C:22]2[N:26]([CH3:27])[C:25]3[CH:28]=[CH:29][C:30]([N:32]4[CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)=[CH:31][C:24]=3[N:23]=2)=[N:19][NH:20][CH:21]=1)=[O:38]

Participants

4

Reactant 2

HCID 887MethanolHCID 178479979HCID 178479979, compound

Product 1

HCID 178479978HCID 178479978, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

{[3-(5-Morpholin-4-yl-methyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl-carbamoyl]-phenyl-methyl}-carbamic acid tert-butyl ester (Example 232) (30 mg) was dissolved in 4M HCl/dioxane, and 3 ml of methanol and stirred at room temperature overnight. The solvent was removed in vacuo and residue triturated with diethylether to give 2-amino-N-[3-(5-morpholin-4-yl-methyl-1H-benzimidazol-2-yl-)-1H-pyrazol-4-yl]-2-phenyl-acetamide (AT8162) as a white solid (20 mg, 83%). (LC/MS (acidic method): Rt 2.39 min, [M+H]+ 432).

Workup

  1. customThe solvent was removed in vacuo and residue
  2. customtriturated with diethylether

Sources & evidence

ORD record
ord-87acb7f95c024927b1f48619981cfd59
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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