Acetic Anhydride → HCID 131730972, compound

HRID 2035508Notes

Reaction equation

HRID 2035508 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:28][CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)=[CH:18][CH:17]=2)[N:12]=[CH:11][C:10]=1[CH2:29][C:30]([NH2:32])=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:33](OC(=O)C)(=[O:35])[CH3:34].O.N>ClCCl>[C:33]([N:25]1[CH2:26][CH2:27][CH2:28][N:22]([C:19]2[CH:18]=[CH:17][C:16]([NH:15][C:13]3[N:12]=[CH:11][C:10]([CH2:29][C:30]([NH2:32])=[O:31])=[C:9]([NH:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH:14]=3)=[CH:21][CH:20]=2)[CH2:23][CH2:24]1)(=[O:35])[CH3:34]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 12896473Azane;hydrateHCID 131730953HCID 131730953, compound2×

Product 1

HCID 131730972HCID 131730972, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

25 mg of 4-(benzylamino)-6-{[4-(1,4-diazepan-1-yl)phenyl]amino}pyridine-3-carboxyamide (the compound of Example 226) was dissolved in 1.5 mL of dichloromethane, to which, under ice cooling, 15.1 mg of acetic anhydride was added, and stirred for 30 minutes. To the reaction mixture 1.5 mL of ammonia water was added, extracted with chloroform, the extract was washed with saturated saline, and dried on anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel thin layer chromatography (chloroform:methanol=10:1), recrystallized from chloroform-methanol-diethylether to obtain 20 mg (73%) of the title compound as light brown needle crystals.

Workup

  1. extractionextracted with chloroform
  2. washthe extract was washed with saturated saline
  3. dry with materialdried on anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel thin layer chromatography (chloroform:methanol=10:1)
  6. customrecrystallized from chloroform-methanol-diethylether

Sources & evidence

ORD record
ord-df692708b6e54fcfabd95b326f641f3e
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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