Hydrochloric Acid → 1-(ethoxycarbonyl)-3-[(4-morpholin-4-ylbenzoyl)amino]-1H-thieno[2,3-c]pyrazole-5-carboxylic acid hydrochloride

HRID 1096156Notes

Reaction equation

HRID 1096156 reaction equation
[N:1]1([C:7]2[CH:35]=[CH:34][C:10]([C:11]([NH:13][C:14]3[C:15]4[CH:26]=[C:25]([C:27]([O:29]C(C)(C)C)=[O:28])[S:24][C:16]=4[N:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:18]=3)=[O:12])=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[ClH:36]>O1CCOCC1>[ClH:36].[CH2:22]([O:21][C:19]([N:17]1[C:16]2[S:24][C:25]([C:27]([OH:29])=[O:28])=[CH:26][C:15]=2[C:14]([NH:13][C:11](=[O:12])[C:10]2[CH:9]=[CH:8][C:7]([N:1]3[CH2:2][CH2:3][O:4][CH2:5][CH2:6]3)=[CH:35][CH:34]=2)=[N:18]1)=[O:20])[CH3:23]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 667847635-tert-butyl 1-ethyl 3-[(4-morpholin-4-ylbenzoyl)amino]-1H-thieno[2,3-c]pyrazole-1,5-dicarboxylate

Product 1

HCID 667857921-(ethoxycarbonyl)-3-[(4-morpholin-4-ylbenzoyl)amino]-1H-thieno[2,3-c]pyrazole-5-carboxylic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5-tert-butyl 1-ethyl 3-[(4-morpholin-4-ylbenzoyl)amino]-1H-thieno[2,3-c]pyrazole-1,5-dicarboxylate (4.05 g) was added to a solution of hydrochloric acid in dioxane (88 mL, 4N solution). The resulting mixture was stirred at room temperature for 72 hours. Afterward, volatiles were removed by evaporation under reduced pressure and the residue triturated with diethyl ether, filtered, extensively washed with diethyl ether and dried under vacuum at 40° C. to give 3.4 g of the title compound, used in the next step without further purification.

Workup

  1. customAfterward, volatiles were removed by evaporation under reduced pressure
  2. customthe residue triturated with diethyl ether
  3. filtrationfiltered
  4. washextensively washed with diethyl ether
  5. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-f4f462ea563344c8b6492849e1454c0b
Source dataset
uspto-grants-2012_03
Patent number
US08138217B2

Reaction notes

Loading…