7-methyl-2-propyl-3-[2'-(aminosulfonyl)[1,1']-biphenyl-4-yl]methyl-6-[(1-oxobutyl)amino]-3H-imidazo[4,5-b]pyridine → 6-amino-7-methyl-2-propyl-3-[2'-(aminosulfonyl)[1,1']-biphenyl-4-yl]methyl-3H-imidazo[4,5-b]pyridine

HRID 36118Notes

Reaction equation

[CH3:1][C:2]1[C:7]([NH:8]C(=O)CCC)=[CH:6][N:5]=[C:4]2[N:14]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[S:33]([NH2:36])(=[O:35])=[O:34])=[CH:23][CH:22]=3)[C:15]([CH2:17][CH2:18][CH3:19])=[N:16][C:3]=12>CO.Cl>[NH2:8][C:7]1[C:2]([CH3:1])=[C:3]2[N:16]=[C:15]([CH2:17][CH2:18][CH3:19])[N:14]([CH2:20][C:21]3[CH:22]=[CH:23][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[S:33]([NH2:36])(=[O:35])=[O:34])=[CH:25][CH:26]=3)[C:4]2=[N:5][CH:6]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 7-methyl-2-propyl-3-[2'-(aminosulfonyl)[1,1']biphenyl-4-yl]methyl-6-[(1-oxobutyl)amino]-3H-imidazo[4,5-b]pyridine (180 mg) in 10 mL of MeOH and 1 mL of conc aqueous HCl was heated to 50° C. for 30 h. The MeOH was removed in vacuo and 100 mL of CH2Cl2 was added. The mixture was washed with saturated aqueous NaHC03 (2×30 mL), dried (Na2SO4), and concentrated to give the title compound as a foam.

Workup

customThe MeOH was removed in vacuo and 100 mL of CH2Cl2
additionwas added
washThe mixture was washed with saturated aqueous NaHC03 (2×30 mL)
dry with materialdried (Na2SO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-e97dca0464ab4c6c8b69dcbd3d005d6c
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05412097

Reaction notes

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