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

HRID 36119

Reaction equation

HRID 36119 reaction equation
[NH2:1][C:2]1[C:3]([CH3:31])=[C:4]2[N:10]=[C:9]([CH2:11][CH2:12][CH3:13])[N:8]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[S:27]([NH2:30])(=[O:29])=[O:28])=[CH:17][CH:16]=3)[C:5]2=[N:6][CH:7]=1.[CH2:32]([S:36](Cl)(=[O:38])=[O:37])[CH2:33][CH2:34][CH3:35].CO>N1C=CC=CC=1>[CH2:32]([S:36]([NH:1][C:2]1[C:3]([CH3:31])=[C:4]2[N:10]=[C:9]([CH2:11][CH2:12][CH3:13])[N:8]([CH2:14][C:15]3[CH:16]=[CH:17][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[S:27]([NH2:30])(=[O:29])=[O:28])=[CH:19][CH:20]=3)[C:5]2=[N:6][CH:7]=1)(=[O:38])=[O:37])[CH2:33][CH2:34][CH3:35]

Participants

5

Reactant 3

HCID 887MethanolHCID 754301-Butanesulfonyl chlorideHCID 199397636-amino-7-methyl-2-propyl-3-[2'-(aminosulfonyl)[1,1']-biphenyl-4-yl]methyl-3H-imidazo[4,5-b]pyridine

Product 1

HCID 199397366-[(Butylsulfonyl)amino]-7-methyl-2-propyl-3-[2'-(aminosulfonyl)[1,1']-biphenyl-4-yl]methyl-3H-imidazo[4,5-b]pyridineYield 60%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 6-amino-7-methyl-2-propyl-3-[2'-(aminosulfonyl)[1,1']biphenyl-4-yl]methyl-3H-imidazo[4,5-b]pyridine (80 mg, 0.15 mmol) in pyridine (0.5 mL) at 0° C. was added butylsulfonyl chloride (0.02 mL, 0.15 mmol). The mixture was stirred for 1 h, then 1 mL of MeOH was added and the mixture was concentrated. Purification (SiO2, 5% MeOH-EtOAc) gave 50 mg of 6-[(Butylsulfonyl)amino]-7-methyl-2-propyl-3-[2'-(aminosulfonyl)[1,1']-biphenyl-4-yl]methyl-3H-imidazo[4,5-b]pyridine as a solid.

Workup

  1. concentrationthe mixture was concentrated
  2. customPurification (SiO2, 5% MeOH-EtOAc)

Sources & evidence

ORD record
ord-34f68061904249758769a9903bb09b3b
Source dataset
uspto-grants-1995_05
Patent number
US05412097

Linked notes

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