Hydrochloric Acid → HCID 67312636, compound

HRID 590312Notes

Reaction equation

HRID 590312 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])=[N:10][C:9]=2[C:17]2[C:18]([F:33])=[C:19]([NH:23][S:24]([C:27]3[N:31]([CH3:32])[N:30]=[CH:29][CH:28]=3)(=[O:26])=[O:25])[CH:20]=[CH:21][CH:22]=2)[CH:5]=[CH:4][N:3]=1.[OH-].[NH4+:35].Cl>CCOC(C)=O>[ClH:1].[NH2:35][C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])=[N:10][C:9]=2[C:17]2[C:18]([F:33])=[C:19]([NH:23][S:24]([C:27]3[N:31]([CH3:32])[N:30]=[CH:29][CH:28]=3)(=[O:26])=[O:25])[CH:20]=[CH:21][CH:22]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 86636598HCID 86636598, compound

Product 1

HCID 67312636HCID 67312636, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N-{3-[5-(2-Chloro-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-1-methyl-1H-pyrazole-5-sulfonamide (530 mg, 1.04 mmol) and ammonium hydroxide (26%, 15 ml) was heated in a steel reactor to 100° C. for 3 h. The reaction mixture was cooled and concentrated under reduced pressure, the residue was dissolved in methanol, and purified by Pre-HPLC (A=10 m MNH4HCO3/H2O, B=Acetonitrile), then the white solid obtained was dissolved in EtOAc, treated with HCl (g) for 30 min. The mixture was concentrated under reduced pressure, and then the residue was suspended in ether (20 ml), treated with ultrasonic for 3 min, filtered, the solid was suspended in ether (20 ml) again, treated with ultrasonic for 3 min, filtered to afford the title compound was obtained as a white solid (142 mg, 26%). 1HNMR (MEOD-d4): δ ppm 8.05 (br s, 1H), 7.61-7.65 (ddd, J1=7.7 Hz, J2=1.6 Hz, 1H), 7.42-7.46 (m, 2H), 7.32-7.36 (t, J=8.0 Hz, 1H), 6.70-6.71 (d, J=2.0 Hz, 1H), 6.25-6.27 (d, J=6.4 Hz, 1H), 4.04 (s, 3H), 1.50 (s, 9H). MS: 488.2 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. dissolutionthe residue was dissolved in methanol
  4. custompurified by Pre-HPLC (A=10 m MNH4HCO3/H2O, B=Acetonitrile), then the white solid
  5. customobtained
  6. concentrationThe mixture was concentrated under reduced pressure
  7. additiontreated with ultrasonic for 3 min
  8. filtrationfiltered
  9. additiontreated with ultrasonic for 3 min
  10. filtrationfiltered

Sources & evidence

ORD record
ord-ac9dfb63cf234889a7d3812e643a1090
Source dataset
uspto-grants-2016_01
Patent number
US09233956B2

Reaction notes

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