Hydrogen Bromide → HCID 66630624, compound

HRID 403034Notes

Reaction equation

HRID 403034 reaction equation
[CH:1]1([NH:4][C:5](=[O:38])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([NH:13][C:14](=[O:37])[C:15]3[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][C:26]([O:29]CC5C=CC=CC=5)=[CH:25][N:24]=4)=[CH:17][CH:16]=3)[CH:7]=2)[CH2:3][CH2:2]1.[BrH:39]>C(O)(=O)C.CCOCC>[BrH:39].[CH:1]1([NH:4][C:5](=[O:38])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([NH:13][C:14](=[O:37])[C:15]3[CH:16]=[CH:17][C:18]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][N:24]=4)=[CH:19][CH:20]=3)[CH:7]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 66631184HCID 66631184, compound

Product 1

HCID 66630624HCID 66630624, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of N-cyclopropyl-4-methyl-3-{[4-(5-benzyloxypyridin-2-ylmethoxy)benzoyl]amino}benzamide (1.0 g, 1.97 mmol) in glacial acetic acid (10 mL) was added a solution of HBr (48% in acetic acid, 30 mL). After 6 hours at 25° C. the solution was diluted with ether (100 mL) and the resultant precipitate filtered off and dried to give the title compound as a pale yellow solid (610 mg, 62%); NMR Spectrum: (DMSOd6) 0.56 (m, 2H), 0.68 (m, 2H), 2.25 (s, 3H), 2.84 (m, 1H), 5.36 (s, 2H), 7.18 (d, 2H), 7.31 (d, 1H), 7.63 (dd, 1H), 7.78-7.84 (m, 3H), 8.00 (d, 2H), 8.36 (m, 2H), 9.86 (s, 1H); Mass Spectrum: M+H+ 418.

Workup

  1. filtrationthe resultant precipitate filtered off
  2. customdried

Sources & evidence

ORD record
ord-13ade02af1aa491c8050cd6b74d31a7f
Source dataset
uspto-grants-2014_06
Patent number
US08742124B2

Reaction notes

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