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Hydrochloric Acid → Methyl [6-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1h-benzimidazol-2-yl]carbamate dihydrochloride salt

HRID 473868
Notes
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Reaction equation

HRID 473868 reaction equation
[CH3:1][O:2][C:3]([NH:5][C:6]1[NH:10][C:9]2[CH:11]=[C:12]([C:15]3[CH:16]=[CH:17][C:18]4[O:24][CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][C:19]=4[CH:32]=3)[CH:13]=[CH:14][C:8]=2[N:7]=1)=[O:4].CO.[ClH:35]>O1CCOCC1.C(OCC)C>[ClH:35].[ClH:35].[O:24]1[C:18]2[CH:17]=[CH:16][C:15]([C:12]3[CH:13]=[CH:14][C:8]4[N:7]=[C:6]([NH:5][C:3](=[O:4])[O:2][CH3:1])[NH:10][C:9]=4[CH:11]=3)=[CH:32][C:19]=2[CH2:20][NH:21][CH2:22][CH2:23]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 675150971,1-dimethylethyl 7-(2-{[(methyloxy)carbonyl]amino}-1H-benzimidazol-6-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

Product 1

HCID 86672024Methyl [6-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1h-benzimidazol-2-yl]carbamate dihydrochloride saltYield 95%

Reagents, catalysts & solvents 2

HCID 3283
Diethyl Ether
Solvent
HCID 312751,4-DioxaneSolvent

Procedure

1,1-Dimethylethyl 7-(2-{[(methyloxy)carbonyl]amino}-1H-benzimidazol-6-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (517 mg, 1.18 mmol) was taken into methanol (2 mL) and 4M hydrogen chloride in dioxane (2 mL) and the mixture was allowed to stand at room temperature for 30 minutes. The suspension obtained was diluted with excess ethyl ether and the solid collected by filtration to give methyl [6-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1H-benzimidazol-2-yl]carbamate dihydrochloride salt (462 mg, 95% yield) as a white solid. MS (EI) for C18H18N4O3: 339 (MH+).

Workup

  1. customThe suspension obtained
  2. filtrationthe solid collected by filtration

Sources & evidence

ORD record
ord-95a8ac83d9ad4a8aaf5e80779ea947a1
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08637499B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes