Hydrochloric Acid → HCID 51352906, compound

HRID 1408528Notes

Reaction equation

HRID 1408528 reaction equation
[CH:1]1([C:4]2[CH:8]=[C:7]([CH:9]3[CH2:11][CH2:10]3)[N:6]([C:12]3[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:26])[C:20]4[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=4)=[CH:14][CH:13]=3)[N:5]=2)[CH2:3][CH2:2]1.C(O)(=O)C1C=CN=CC=1.[ClH:36]>C1COCC1.C(OCC)C>[ClH:36].[CH:1]1([C:4]2[CH:8]=[C:7]([CH:9]3[CH2:11][CH2:10]3)[N:6]([C:12]3[CH:13]=[CH:14][C:15]([NH:18][C:19](=[O:26])[C:20]4[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=4)=[CH:16][CH:17]=3)[N:5]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5922Isonicotinic AcidHCID 51352907HCID 51352907, compound

Product 1

HCID 51352906HCID 51352906, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure-1 N-[4-(3,5-dicyclopropyl-1H-pyrazol-1-yl)phenyl] isonicotinamide (40 mg) was prepared from isonicotinic acid (74 mg, 0.60 mmol) and intermediate 27 (120 mg, 0.50 mmol) as a pale yellow solid and dissolved in THF. Saturated HCl in diethyl ether was added to this solution at 0° C. and stirred for 15 min Solid that separated out was filtered and dried to give the title compound (47 mg) as an yellow solid. M.P. 232-238° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 11.08 (s, 1H), 9.01 (d, J 6.0, 2H), 8.30 (d, J 6.0, 2H), 7.94 (d, J 8.8, 2H), 7.61 (d, J 8.8, 2H), 5.83 (s, 1H), 1.90-1.74 (m, 2H), 0.95-0.80 (m, 4H), 0.70-0.60 (m, 4H). MS (m/z): 345.22 [M−H−HCl]−.

Workup

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

Sources & evidence

ORD record
ord-df3cab8d8a5b43f6827490451a62e3db
Source dataset
uspto-grants-2014_12
Patent number
US08921364B2

Reaction notes

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