Hydrochloric Acid → HCID 67114804, compound

HRID 388846Notes

Reaction equation

HRID 388846 reaction equation
[CH:1]1([C:4]2[N:8]([C:9]3[N:14]=[CH:13][C:12]([NH:15][C:16](=[O:23])[C:17]4[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=4)=[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.C(O)(=O)C1C=CN=CC=1.[ClH:37]>C1COCC1.C(OCC)C>[ClH:37].[CH:1]1([C:4]2[N:8]([C:9]3[N:14]=[CH:13][C:12]([NH:15][C:16](=[O:23])[C:17]4[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=4)=[CH:11][CH:10]=3)[N:7]=[C:6]([C:24]([F:27])([F:25])[F:26])[CH:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5922Isonicotinic AcidHCID 57518353HCID 57518353, compound

Product 1

HCID 67114804HCID 67114804, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure-1, N-{6-[5-cyclopropyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]pyridin-3-yl}isonicotinamide (160 mg) was prepared from isonicotinic acid (132 mg, 1.2 mmol) and intermediate 36 (290 mg, 0.67 mmol) as an off-white 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 (137 mg) as an yellow solid M.P.: 186-188° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 11.23 (s, 1H), 8.99 (d, J 2.5, 1H), 8.94 (d, J 6.2, 2H), 8.47 (dd, J 2.5, 8.8, 1H), 8.14 (d, J 6.2, 2H), 7.85 (d, J 8.8, 1H), 6.65 (s, 1H), 2.60-2.50 (m, 1H), 1.04-0.94 (m, 2H), 0.80-0.73 (m, 2H). MS (m/z): 371.65 [M−H]−.

Workup

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

Sources & evidence

ORD record
ord-b81aef9256fb49a0ab80a51d1674c1cd
Source dataset
uspto-grants-2013_02
Patent number
US08377970B2

Reaction notes

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