Hydrochloric Acid → 2-({[4-({[5-(Carboxymethyl)-1-oxo-1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl]acetyl}amino)cyclohexyl]methyl}amino)-1H-benzimidazole hydrochloride

HRID 1179340Notes

Reaction equation

HRID 1179340 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19](=[O:41])[CH2:20][N:21]2[CH2:27][CH2:26][CH:25]([CH2:28][C:29]([O:31]C(C)(C)C)=[O:30])[C:24]3[CH:36]=[CH:37][CH:38]=[CH:39][C:23]=3[C:22]2=[O:40])[CH2:14][CH2:13]1.[ClH:42]>C(O)(=O)C.O1CCOCC1>[ClH:42].[C:29]([CH2:28][CH:25]1[C:24]2[CH:36]=[CH:37][CH:38]=[CH:39][C:23]=2[C:22](=[O:40])[N:21]([CH2:20][C:19]([NH:18][CH:15]2[CH2:14][CH2:13][CH:12]([CH2:11][NH:10][C:2]3[NH:1][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=3)[CH2:17][CH2:16]2)=[O:41])[CH2:27][CH2:26]1)([OH:31])=[O:30]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86591658tert-Butyl {2-[2-({4-[(1H-benzimidazol-2-ylamino)methyl]-cyclohexyl}amino)-2-oxoethyl]-1-oxo-2,3,4,5-tetrahydro-1H-2-benzazepin-5-yl}acetate

Product 1

HCID 865916592-({[4-({[5-(Carboxymethyl)-1-oxo-1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl]acetyl}amino)cyclohexyl]methyl}amino)-1H-benzimidazole hydrochloride

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Analogously to Example II, the t-butyl ester (Example V) in glacial acetic acid was cleaved using 4N HCl in dioxane. After freeze-drying, 0.45 g of white amorphous hydrochloride remained; ESI-MS [M+H+]: 504.

Workup

  1. customAfter freeze-drying

Sources & evidence

ORD record
ord-3c061b41f8a44b4c806401cb8b9dd7d3
Source dataset
uspto-grants-2007_10
Patent number
US07279468B2

Reaction notes

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