Pyridine → HCID 131731000, compound

HRID 2035532Notes

Reaction equation

HRID 2035532 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:19]=[CH:18][C:17]([CH2:20][C:21]([NH2:23])=[O:22])=[C:16]([NH:24][CH2:25][CH:26]4[CH2:30][CH2:29][CH2:28][NH:27]4)[CH:15]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[C:31](OC(=O)C)(=[O:33])[CH3:32].N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.O>[C:31]([N:27]1[CH2:28][CH2:29][CH2:30][CH:26]1[CH2:25][NH:24][C:16]1[CH:15]=[C:14]([NH:13][C:10]2[CH:11]=[CH:12][C:7]([N:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)=[CH:8][CH:9]=2)[N:19]=[CH:18][C:17]=1[CH2:20][C:21]([NH2:23])=[O:22])(=[O:33])[CH3:32]

Participants

7

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 131730997HCID 131730997, compound2×

Product 1

HCID 131731000HCID 131731000, compoundYield 87.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

30.3 mg of 6-[(4-morpholinophenyl)amino]-4-[(pyrrolidin-2-ylmethyl)amino]pyridine-3-carboxyamide (the compound of Example 358) was dissolved in 2 mL of methylene chloride, to which 9.4 mg of acetic anhydride and 9.1 mg of pyridine were sequentially added, and stirred at room temperature for 2 hours. To the reaction mixture saturated sodium bicarbonate in water was added, extracted with chloroform:methanol=10:1, 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:ammonia methanol=8:1), recrystallized from chloroform-ether to obtain the title compound (29.3 mg, 87%) as a light yellow crystalline powder.

Workup

  1. additionwere sequentially added
  2. extractionextracted with chloroform
  3. washmethanol=10:1, the extract was washed with saturated saline
  4. dry with materialdried on anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel thin layer chromatography (chloroform:ammonia methanol=8:1)
  7. customrecrystallized from chloroform-ether

Sources & evidence

ORD record
ord-c34d3075c05a4ac39b382900b3e21058
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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