Hydrochloric Acid → HCID 67042520, compound

HRID 521798Notes

Reaction equation

HRID 521798 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[NH:9][C:10]([NH:12][C:13]1[CH:34]=[CH:33][C:16]([O:17][C:18]2[CH:23]=[CH:22][N:21]=[C:20]([C:24]3[CH:25]=[C:26]([C:29]([O:31]C)=[O:30])[S:27][CH:28]=3)[CH:19]=2)=[CH:15][CH:14]=1)=[O:11].[OH-].[Na+].Cl>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[NH:9][C:10]([NH:12][C:13]1[CH:14]=[CH:15][C:16]([O:17][C:18]2[CH:23]=[CH:22][N:21]=[C:20]([C:24]3[CH:25]=[C:26]([C:29]([OH:31])=[O:30])[S:27][CH:28]=3)[CH:19]=2)=[CH:33][CH:34]=1)=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67042545HCID 67042545, compound

Product 1

HCID 67042520HCID 67042520, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
66 °C

Procedure

To a stirred solution of methyl 4-{4-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}thiophene-2-carboxylate (550 mg, 1.15 mmol) in a mixture of solvents—THF/MeOH (20 ml/20 ml) was added 1 ml of 5M NaOH (5 mmol) solution. The mixture was heated in a 66° C. bath for 2 hours, cooled to room temperature and poured into 200 ml of water. 2M HCl was added until pH=5. The resulting precipitates were filtered, washed with water, and dried in vacuo to give 4-{4-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}thiophene-2-carboxylic acid as off-white solid. Yield: 520 mg, 97%.

Workup

  1. temperaturecooled to room temperature
  2. customThe resulting precipitates
  3. filtrationwere filtered
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-941be03ef32040d0ac5e07207eb10092
Source dataset
uspto-grants-2016_05
Patent number
US09328103B2

Reaction notes

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