Hydrochloric Acid → (S)-1-(3-(difluoromethoxy)phenyl)-N-(2-fluoro-4-(morpholin-2-yl)phenyl)-1H-pyrazole-4-carboxamide hydrochloride

HRID 571845Notes

Reaction equation

HRID 571845 reaction equation
[F:1][CH:2]([F:38])[O:3][C:4]1[CH:5]=[C:6]([N:10]2[CH:14]=[C:13]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([C@@H:24]4[O:29][CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25]4)=[CH:20][C:19]=3[F:37])=[O:16])[CH:12]=[N:11]2)[CH:7]=[CH:8][CH:9]=1.[ClH:39].CCOCC>O1CCOCC1>[ClH:39].[F:38][CH:2]([F:1])[O:3][C:4]1[CH:5]=[C:6]([N:10]2[CH:14]=[C:13]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([C@@H:24]4[O:29][CH2:28][CH2:27][NH:26][CH2:25]4)=[CH:20][C:19]=3[F:37])=[O:16])[CH:12]=[N:11]2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 71086889(S)-tert-Butyl 2-(4-(1-(3-(difluoromethoxy)phenyl)-1H-pyrazole-4-carboxamido)-3-fluorophenyl)morpholine-4-carboxylate

Product 1

HCID 71087039(S)-1-(3-(difluoromethoxy)phenyl)-N-(2-fluoro-4-(morpholin-2-yl)phenyl)-1H-pyrazole-4-carboxamide hydrochlorideYield 91%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
60 °C

Procedure

(S)-tert-butyl 2-(4-(1-(3-(difluoromethoxy)phenyl)-1H-pyrazole-4-carboxamido)-3-fluorophenyl)morpholine-4-carboxylate (102 mg, 0.2 mmol) was dissolved in dioxane (0.75 ml) and a solution of HCl in dioxane (4M, 0.75 ml, 3 mmol) was added. The reaction mixture was stirred for 90 min at 60° C. After cooling ether was added, the solid was filtered off, washed with ether and dried in vacuo at 60° C. to afford (S)-1-(3-(difluoromethoxy)phenyl)-N-(2-fluoro-4-(morpholin-2-yl)phenyl)-1H-pyrazole-4-carboxamide hydrochloride (84 mg, 91%) as a white solid. MS (ISP): 433.2 ([M+H]+).

Workup

  1. additionwas added
  2. filtrationthe solid was filtered off
  3. washwashed with ether
  4. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-53054507b8b54155b2b87a8fdb88fa76
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

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