Hydrochloric Acid → HCID 71542907, compound

HRID 1402534Notes

Reaction equation

HRID 1402534 reaction equation
C([O:3][CH:4](OCC)[CH2:5][NH:6][C:7]([C:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[C:18]([O:20][C:21]3[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH:30][C:31]4[CH:36]=[C:35]([CH3:37])[CH:34]=[CH:33][C:32]=4[F:38])=[O:29])=[CH:23][CH:22]=3)[CH:17]=[CH:16][N:15]=2)[NH:11][CH:10]=1)=[O:8])C.Cl.O.C([O-])(O)=O.[Na+]>C1COCC1>[F:38][C:32]1[CH:33]=[CH:34][C:35]([CH3:37])=[CH:36][C:31]=1[NH:30][C:28]([NH:27][C:24]1[CH:23]=[CH:22][C:21]([O:20][C:18]2[CH:17]=[CH:16][N:15]=[C:14]([C:12]3[NH:11][CH:10]=[C:9]([C:7]([NH:6][CH2:5][CH:4]=[O:3])=[O:8])[CH:13]=3)[CH:19]=2)=[CH:26][CH:25]=1)=[O:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 71542908HCID 71542908, compound

Product 1

HCID 71542907HCID 71542907, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of N-(2,2-diethoxyethyl)-5-{4-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}1H-pyrrole-3-carboxamide (580 mg, 1.03 mmol) in 10 ml of THF was added 1 ml of 2M HCl. The mixture was heated under nitrogen at 60 C. for 2 hours, cooled to room temperature, and poured into 100 ml of water. Saturated NaHCO3 solution was added until pH=8. The precipitates were filtered, washed with water, and dried in vacuo to give 5-{4-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}-N-(2-oxoethyl)-1H-pyrrole-3-carboxamide as light brown solid. Yield: 450 mg, 90%.

Workup

  1. temperatureThe mixture was heated under nitrogen at 60 C
  2. filtrationThe precipitates were filtered
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-db647b5299194c1c8557f048b1775212
Source dataset
uspto-grants-2014_12
Patent number
US08906944B2

Reaction notes

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