Hydrochloric Acid → HCID 67198960, compound

HRID 1408538Notes

Reaction equation

HRID 1408538 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[N: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].[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[N:17]=[CH:16][C:15]([NH:18][C:19](=[O:26])[C:20]4[CH:21]=[CH:22][N:23]=[CH:24][CH:25]=4)=[CH:14][CH:13]=3)[N:5]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5922Isonicotinic AcidHCID 51353106HCID 51353106, compound

Product 1

HCID 67198960HCID 67198960, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure-1, N-[6-(3,5-dicyclopropyl-1H-pyrazol-1-yl)pyridin-3-yl]isonicotinamide (220 mg) from intermediate 30 (200 mg, 0.83 mmol) and isonicotinic acid (163 mg, 1.3 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 (190 mg) as a pale-yellow solid. M.P.: 200.3-202.4° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 11.26 (s, 1H), 8.99 (t, J 5.4, 2H), 8.88 (s, 1H), 8.35 (dd, J 2.6, 6.3, 1H), 8.30-8.25 (m, 2H), 7.78 (d, J 8.9, 1H), 5.83 (s, 1H), 2.72-2.62 (m, 1H), 1.90-1.81 (m, 1H), 0.94-0.82 (m, 4H), 0.70-0.59 (m, 4H). MS (m/z): 346.13 [M+H−2HCl]+.

Workup

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

Sources & evidence

ORD record
ord-5d856d0e57b74b88bf445b48bfae0ce0
Source dataset
uspto-grants-2014_12
Patent number
US08921364B2

Reaction notes

Loading…