Water → HCID 131730941, compound

HRID 2035489Notes

Reaction equation

HRID 2035489 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][CH:32]=1)[CH2:5][NH:6][C:7]1[CH:12]=[C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[CH:16][CH:15]=2)[N:10]=[CH:9][C:8]=1[CH2:26][C:27]([NH2:29])=[O:28].[C:33](OC(=O)C)(=[O:35])[CH3:34].O>N1C=CC=CC=1>[C:33]([NH:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][CH:32]=1)[CH2:5][NH:6][C:7]1[CH:12]=[C:11]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[CH:18][CH:19]=2)[N:10]=[CH:9][C:8]=1[CH2:26][C:27]([NH2:29])=[O:28])(=[O:35])[CH3:34]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 131730939HCID 131730939, compound2×

Product 1

HCID 131730941HCID 131730941, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

22 mg of 4-[(3-aminobenzyl)amino]-6-[(4-morpholinophenyl)amino]pyridine-3-carboxyamide (the compound of Example 103) was dissolved in 0.5 mL of pyridine, to which 5.4 mg of acetic anhydride was added, and stirred at room temperature for 4 hours. To the reaction mixture, water was added, stirred, and the solvent was evaporated. The residue was purified by silica gel thin layer chromatography (chloroform: methanol=10:1) to obtain 2.6 mg (11%) of 4-{[3-(acetylamino)benzyl]amino}-6-[(4-morpholinophenyl)amino]pyridine-3-carboxyamide (Example 104-1) as a white solid. Furthermore, 11.6 mg (44%) of 4-{[3-(acetylamino)benzyl]amino}-6-[acetyl(4-morpholinophenyl)amino]pyridine-3-carboxyamide (Example 104-2) was obtained as a yellowish brown oil.

Workup

  1. additionwas added
  2. stirringstirred
  3. customthe solvent was evaporated
  4. customThe residue was purified by silica gel thin layer chromatography (chloroform: methanol=10:1)

Sources & evidence

ORD record
ord-04dfdc0d0c454bae9b91ac702c88b937
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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