Acetic Anhydride → HCID 15718840, compound

HRID 2166147Notes

Reaction equation

HRID 2166147 reaction equation
[CH2:1]([NH:3][CH2:4][CH2:5][N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[N:8]=[C:7]1[NH:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:18][CH2:17]1)[CH3:2].[C:29](OC(=O)C)(=[O:31])[CH3:30]>ClC(Cl)Cl>[CH2:1]([N:3]([CH2:4][CH2:5][N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[N:8]=[C:7]1[NH:15][CH:16]1[CH2:17][CH2:18][N:19]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:20][CH2:21]1)[C:29](=[O:31])[CH3:30])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 15718983HCID 15718983, compound

Product 1

HCID 15718840HCID 15718840, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

7.8 Parts of N-ethyl-2-[[1-(phenylmethyl)-4-piperidinyl]amino]-3H-imidazo[4,5-b]pyridin-3-ethanamine were taken up in 75 parts of trichloromethane. 1.51 Parts of acetic acid anhydride were added (exothermic reaction). The reaction mixture was stirred for 18 hours at room temperature. The whole was filtered over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was taken up in methylbenzene and the whole was evaporated again, yielding 8.5 parts (100%) of N-ethyl-N-[2-[2-[[1-(phenylmethyl)-4-piperidinyl]amino]-3H-imidazo[4,5-b]pyridin-3-yl]ethyl]acetamide as a residue (compound 176).

Workup

  1. custom(exothermic reaction)
  2. filtrationThe whole was filtered over silica gel using
  3. additiona mixture of trichloromethane and methanol
  4. customThe pure fractions were collected
  5. customthe eluent was evaporated
  6. customthe whole was evaporated again

Sources & evidence

ORD record
ord-0de6a14479c84caaa94e79e413f41668
Source dataset
uspto-grants-1990_07
Patent number
US04943580

Reaction notes

Loading…