N-[4-Methoxy-3-(4-bromophenyl)aminocarbonyl-phenyl]-2-chloro-5-(tert-butoxycarbonylamino)methyl-benzamide → N-[4-Methoxy-3-(4-bromophenyl)aminocarbonyl-phenyl]-2-chloro-5-aminomethyl-benzamide

HRID 1846096Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:27])[C:11]2[CH:16]=[C:15]([CH2:17][NH:18]C(OC(C)(C)C)=O)[CH:14]=[CH:13][C:12]=2[Cl:26])=[CH:5][C:4]=1[C:28]([NH:30][C:31]1[CH:36]=[CH:35][C:34]([Br:37])=[CH:33][CH:32]=1)=[O:29]>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:27])[C:11]2[CH:16]=[C:15]([CH2:17][NH2:18])[CH:14]=[CH:13][C:12]=2[Cl:26])=[CH:5][C:4]=1[C:28]([NH:30][C:31]1[CH:32]=[CH:33][C:34]([Br:37])=[CH:35][CH:36]=1)=[O:29]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2.66 g N-[4-methoxy-3-(4-bromophenyl)aminocarbonyl-phenyl]-2-chloro-5-(tert.butoxycarbonylamino)methyl-benzamide (4.51 mmol) 25 mL 4M HCl in dioxane and 50 mL dioxane was stirred for 2 h at rt and 60 min at 50° C. and concentrated i.vac. to furnish the subtitle compound. Yield: (quantitative). MS [M+H]+=488 (Br/Cl-isotope pattern).

Workup

concentrationconcentrated i.vac

Sources & evidence

ORD record: ord-2d845f58350c44959165526c96fb560a
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08951999B2

Reaction notes

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