Acetic Acid → 5,7-dimethyl-2-ethyl-3-[2'-(N-cyanoaminosulfonyl)[1,1']-biphenyl-4-yl]methyl-3H-imidazo[4,5-b]pyridine

HRID 36105Notes

Reaction equation

HRID 36105 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[S:26]([NH2:29])(=[O:28])=[O:27])=[CH:16][CH:15]=3)[C:9]([CH2:11][CH3:12])=[N:10][C:5]2=[C:4]([CH3:30])[CH:3]=1.CC1(C)[SiH2][SiH]=[N:35][C:34](C)(C)C1(C)C.[Na].BrC#N.CC(O)=O>C1COCC1>[CH3:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:13][C:14]3[CH:15]=[CH:16][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[S:26]([NH:29][C:34]#[N:35])(=[O:27])=[O:28])=[CH:18][CH:19]=3)[C:9]([CH2:11][CH3:12])=[N:10][C:5]2=[C:4]([CH3:30])[CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 10476Cyanogen BromideHCID 103420975,7-dimethyl-2-ethyl-3-[2'-(aminosulfonyl)[1,1']-biphenyl-4-yl]methyl-3H-imidazo[4,5-b]pyridineHCID 131718990Sodium hexamethyldisilazine

Product 1

HCID 152363195,7-dimethyl-2-ethyl-3-[2'-(N-cyanoaminosulfonyl)[1,1']-biphenyl-4-yl]methyl-3H-imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a stirred solution of 5,7-dimethyl-2-ethyl-3-[2'-(aminosulfonyl)[1,1']-biphenyl-4-yl]methyl-3H-imidazo[4,5-b]pyridine (122 mg, 0.29 mmol) in THF (1.5 mL) at 0° C. was added sodium hexamethyldisilazine (0.35 mL of a 1M solution in THF). After 10 min, a solution of BrCN (37 mg, 0.35 mmol) in THF (1 ml) was added dropwise via a double tipped needle. The reaction was warmed to r.t. and stirred for 3 h at which time 0.3 mL of HOAc was added. Extraction with CH2Cl2 (5×30 mL) from H2O (30 mL), evaporation of the organic extracts and purification (SiO2, 80:19:1 CH2Cl2 /CH3OH/NH4OH) gave 5,7-dimethyl-2-ethyl-3-[2'-(N-cyanoaminosulfonyl)[1,1']-biphenyl-4-yl]methyl-3H-imidazo[4,5-b]pyridine as a glass.

Workup

  1. additionwas added
  2. extractionExtraction with CH2Cl2 (5×30 mL)
  3. customfrom H2O (30 mL), evaporation of the organic extracts and purification (SiO2, 80:19:1 CH2Cl2 /CH3OH/NH4OH)

Sources & evidence

ORD record
ord-f922ee9d1e5a49cfa91dca9b5ff4a135
Source dataset
uspto-grants-1995_05
Patent number
US05412097

Reaction notes

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