Benzoyl chloride → HCID 19939733, compound

HRID 36120Notes

Reaction equation

HRID 36120 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.C1COCC1.CN(C=O)C.[C:42](Cl)(=[O:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>CO>[C:42]([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:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 199397636-amino-7-methyl-2-propyl-3-[2'-(aminosulfonyl)[1,1']-biphenyl-4-yl]methyl-3H-imidazo[4,5-b]pyridineHCID 21974620tetrahydrofuran N,N-dimethylformamide

Product 1

HCID 19939733HCID 19939733, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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 (189 mg, 0.435 mmol) in 14:1 THF/DMF (7.5 mL) at -15° C. was added benzoyl chloride (0.045 mL, 0.392 mmol). The mixture was stirred for 12 h, then 1 mL of MeOH was added and the mixture was o concentrated. Purification (SiO2, 93:3:4 CH2Cl2/MeOH/HOAc) gave the title compound as a solid.

Workup

  1. concentrationconcentrated
  2. customPurification (SiO2, 93:3:4 CH2Cl2/MeOH/HOAc)

Sources & evidence

ORD record
ord-ae0560f1471f45d5bc05fcd277e33686
Source dataset
uspto-grants-1995_05
Patent number
US05412097

Reaction notes

Loading…