Hydrochloric Acid → HCID 67198909, compound

HRID 1408550Notes

Reaction equation

HRID 1408550 reaction equation
[CH:1]1([C:4]2[N:8]([C:9]3[N:14]=[CH:13][C:12]([NH:15][C:16](=[O:24])[C:17]4[CH:22]=[CH:21][CH:20]=[N:19][C:18]=4[CH3:23])=[CH:11][CH:10]=3)[N:7]=[C:6]([C:25]([F:28])([F:27])[F:26])[CH:5]=2)[CH2:3][CH2:2]1.CC1N=CC=CC=1C(O)=O.[ClH:39]>C1COCC1.C(OCC)C>[ClH:39].[CH:1]1([C:4]2[N:8]([C:9]3[N:14]=[CH:13][C:12]([NH:15][C:16](=[O:24])[C:17]4[CH:22]=[CH:21][CH:20]=[N:19][C:18]=4[CH3:23])=[CH:11][CH:10]=3)[N:7]=[C:6]([C:25]([F:28])([F:27])[F:26])[CH:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6433732-Methylnicotinic acidHCID 57518352HCID 57518352, compound

Product 1

HCID 67198909HCID 67198909, 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}-2-methylnicotinamide (35 mg) was prepared from 2-methylnicotinic acid (110 mg, 0.80 mmol) and intermediate 36 (150 mg, 0.5 mmol) as a 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 (20 mg) as a white solid. M.P.: 241-245° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 11.15 (s, 1H), 8.89 (d, J 2.5, 1H), 8.74 (d, J 4.1 1H), 8.42 (dd, J 2.6, 8.8, 1H), 8.32 (d, J 7.7, 1H), 7.83 (d, J 8.8, 1H), 7.72-7.64 (m, 1H), 6.65 (s, 1H), 2.70 (s, 3H), 2.58-2.50 (m, 1H), 1.00-0.95 (m, 2H), 0.81-0.76 (m, 2H). MS (m/z): 385.64 [M−H−HCl]−.

Workup

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

Sources & evidence

ORD record
ord-b340fa87f4f346ea8c31a7777e8ac29a
Source dataset
uspto-grants-2014_12
Patent number
US08921364B2

Reaction notes

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