HCID 131730954, compound → HCID 131730953, compound

HRID 2035496Notes

Reaction equation

HRID 2035496 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][N:25](C(=O)C(F)(F)F)[CH2:24][CH2:23]3)=[CH:18][CH:17]=2)[N:12]=[CH:11][C:10]=1[CH2:35][C:36]([NH2:38])=[O:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.O1CCCC1.[OH-].[Na+].O>[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([N:22]3[CH2:28][CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)=[CH:20][CH:21]=2)[N:12]=[CH:11][C:10]=1[CH2:35][C:36]([NH2:38])=[O:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 1

HCID 131730954HCID 131730954, compound

Product 1

HCID 131730953HCID 131730953, compoundYield 83%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

386 mg of 4-(benzylamino)-6-{[4-(4-trifluoroacetyl-1,4-diazepan-1-yl)phenyl]amino}pyridine-3-carboxyamide (the compound of Example 213) was dissolved in a mixture of 10 mL of methanol and 10 mL of tetrahydrofuran, to which 2 mL of 2 mol/L sodium hydroxide in water was added at room temperature and stirred for 1 hour. The reaction mixture was concentrated, the residue was dissolved in chloroform, washed with water and saturated saline, and dried on anhydrous sodium sulfate. The solvent was evaporated, and the residue was crystallized from chloroform-methanol-diethylether to obtain 260 mg (83%) of the title compound as light brown needle crystals.

Workup

  1. additionwas added at room temperature
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in chloroform
  4. washwashed with water and saturated saline
  5. dry with materialdried on anhydrous sodium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was crystallized from chloroform-methanol-diethylether

Sources & evidence

ORD record
ord-c0afd91a562c42c68792f3ad84e61951
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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