Hydrochloric Acid → HCID 57518319, compound

HRID 388837Notes

Reaction equation

HRID 388837 reaction equation
[CH:1]1([C:4]2[N:8]([C:9]3[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]4[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=4)=[O:17])=[CH:11][CH:10]=3)[N:7]=[C:6]([C:24]([F:27])([F:26])[F:25])[CH:5]=2)[CH2:3][CH2:2]1.N1C=CC(C(O)=O)=CC=1.[ClH:37]>C1COCC1.C(OCC)C>[ClH:37].[CH:1]1([C:4]2[N:8]([C:9]3[CH:10]=[CH:11][C:12]([NH:15][C:16]([C:18]4[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=4)=[O:17])=[CH:13][CH:14]=3)[N:7]=[C:6]([C:24]([F:25])([F:26])[F:27])[CH:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5922Isonicotinic AcidHCID 57518320HCID 57518320, compound

Product 1

HCID 57518319HCID 57518319, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Following general procedure-1, N-{4-[5-cyclopropyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl}pyridine-4-carboxamide (120 mg) was prepared from pyridine-4-carboxylic acid (66 mg, 0.54 mmol) and intermediate 31 (120 mg, 0.45 mmol) as a pale yellow solid and dissolved in THF. Saturated HCl in diethyl ether was added at 0° C. to it and stirred for 15 min Solid that separated out was filtered and dried to give the title compound (70 mg) as a yellow solid. M.P. 210-215° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 10.90 (s, 1H), 8.90 (d, J 5.40, 2H), 8.07 (d, J 5.40, 2H), 7.99 (d, J 8.8, 2H), 7.66 (d, J 8.8, 2H), 6.62 (s, 1H), 1.86-1.82 (m, 1H), 0.99-0.95 (m, 2H), 0.83-0.79 (m, 2H). MS (m/z): 406.89 [M−H]−.

Workup

  1. customthat separated out
  2. filtrationwas filtered
  3. customdried

Sources & evidence

ORD record
ord-d3d9997f082d4cc09ee5c47feca5ae61
Source dataset
uspto-grants-2013_02
Patent number
US08377970B2

Reaction notes

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