Hydrochloric Acid → HCID 57476901, compound

HRID 2368443Notes

Reaction equation

HRID 2368443 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][C:12](=[O:26])[C:13]([NH:16][C:17](=[O:25])[C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)([CH3:15])[CH3:14])=[N:8][C:7]=1[C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1)=[O:5])C.[OH-].[K+].Cl>CCO.O>[F:24][C:21]1[CH:20]=[CH:19][C:18]([C:17]([NH:16][C:13]([CH3:14])([CH3:15])[C:12]([NH:11][C:9]2[S:10][C:6]([C:4]([OH:5])=[O:3])=[C:7]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[N:8]=2)=[O:26])=[O:25])=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 57513749HCID 57513749, compound

Product 1

HCID 57476901HCID 57476901, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of Ethyl-2-(2-(4-fluorobenzamido)-2-methylpropanamido)-4-(4-fluorophenyl)thiazole-5-carboxylate (4.3 g, 9 mmol) in EtOH (25 mL) was added KOH (1 eq) in water (25 mL). The reaction was stirred at 65 C for 15 hours followed by stirring at room temperature over 3 days. It was then acidified with 1 N HCl and the resulting precipitates were collected by filtration and dried to afford the title compound. 1H NMR (400 MHz, DMSO-d6) ppm 1.53 (s, 6H) 7.20 (t, J=8.97 Hz, 2H) 7.32 (t, J=8.84 Hz, 2H) 7.70 (dd, J=8.72, 5.68 Hz, 2H) 8.03 (dd, J=8.72, 5.56 Hz, 2H) 8.64 (s, 1H) 12.43 (s, 1H) 12.94 (br. s., 1H). MS m/z 446 (M+H), 444 (M−1).

Workup

  1. stirringby stirring at room temperature over 3 days
  2. customthe resulting precipitates
  3. filtrationwere collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-46a1336e398940d79dd0e13fdf5f231a
Source dataset
uspto-grants-2014_04
Patent number
US08703761B2

Reaction notes

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