Hydrochloric Acid → 3-Cyano-5-[(1H-indazol-4-ylmethyl)-carbamoyl]-thiophene-2-carboxylic acid

HRID 1952655Notes

Reaction equation

HRID 1952655 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:12](=[O:24])[NH:13][CH2:14][C:15]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:16]=2[CH:17]=[N:18][NH:19]3)=[CH:8][C:9]=1[C:10]#[N:11])=[O:4].O.[OH-].[Li+].C1COCC1.Cl>O>[C:10]([C:9]1[CH:8]=[C:7]([C:12](=[O:24])[NH:13][CH2:14][C:15]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:16]=2[CH:17]=[N:18][NH:19]3)[S:6][C:5]=1[C:3]([OH:4])=[O:2])#[N:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 682266533-Cyano-5-[(1H-indazol-4-ylmethyl)-carbamoyl]-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 682269853-Cyano-5-[(1H-indazol-4-ylmethyl)-carbamoyl]-thiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-Cyano-5-[(1H-indazol-4-ylmethyl)-carbamoyl]-thiophene-2-carboxylic acid methyl ester (262.7 mg, 0.77 mmol), lithium hydroxide monohydrate (250 mg, 6.17 mmol), THF (8 mL) and water (10 mL) was stirred 4 h, acidified with 1N HCl and extracted with EtOAc (×3). The organic extracts were combined, washed with brine, dried over sodium sulfate, filtered and evaporated to give the title compound, 0.1369 g (54%). MS m/e 327.0 (M+H+).

Workup

  1. extractionextracted with EtOAc (×3)
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-3845c5c296d84acba57c9f6e11e25265
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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