Ammonia → HCID 178428702, compound

HRID 2250385Notes

Reaction equation

HRID 2250385 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9](/[CH:11]=[CH:12]/[C:13]3[N:18]=[C:17]([NH:19]C(=O)C)[CH:16]=[C:15]([CH3:23])[CH:14]=3)[NH:8][C:5]2=[N:6][CH:7]=1.N>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9](/[CH:11]=[CH:12]/[C:13]3[N:18]=[C:17]([NH2:19])[CH:16]=[C:15]([CH3:23])[CH:14]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 178474147HCID 178474147, compound

Product 1

HCID 178428702HCID 178428702, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

1.20 g of N-{6-[(E)-2-(6-bromo-3H-imidazo[4,5-b]pyridin-2-yl)-vinyl]-4-methyl-pyridin-2-yl}-acetamide (compound B10) are suspended in 12 ml of aqueous sulphuric acid (10% strength) at 115° C. for 17 h. Subsequently, the mixture is cooled to 0° C. and conc. aqueous ammonia is added until pH=10. Thereafter, the mixture is extracted 3 times each with 70 ml of ethyl acetate. The combined organic layers are dried using sodium sulphate, filtered with suction, and evaporated to dryness to yield 880 mg of the title compound as an oil, which solidifies upon standing. M.p. 280° C. ESI-MS: 330.2/332.2 (MH+; 100%/90%). TLC: Rf=0.35 (dichloromethane/methanol 10:1).

Workup

  1. extractionThereafter, the mixture is extracted 3 times each with 70 ml of ethyl acetate
  2. customThe combined organic layers are dried
  3. filtrationfiltered with suction
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-5ae0b310ea644e949f412bc0f4e06f5a
Source dataset
uspto-grants-2008_01
Patent number
US07317021B2

Reaction notes

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