Hydrochloric Acid → HCID 57518315, compound

HRID 388833Notes

Reaction equation

HRID 388833 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][CH:23]=[N:22][CH:21]=4)=[CH:14][CH:13]=3)[N:5]=2)[CH2:3][CH2:2]1.C(O)(=O)C1C=CC=NC=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:25]=[CH:24][CH:23]=[N:22][CH:21]=4)=[CH:14][CH:13]=3)[N:5]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 938Nicotinic AcidHCID 57518316HCID 57518316, compound

Product 1

HCID 57518315HCID 57518315, 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]nicotinamide (82 mg) was prepared from intermediate 30 (120 mg, 0.5 mmol) and nicotinic acid (98 mg, 0.65 mmol) as a 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 (80 mg) as an yellow solid. M.P.: 164.6-169.5° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 11.19 (s, 1H), 9.36 (s, 1H), 8.95 (d, J 5.2, 1H), 8.88 (d, J 2.5, 1H), 8.75 (d, J 8, 1H), 8.36 (dd, J 2.5, 8.9, 1H), 7.92 (dd, J 5.3, 8, 1H), 7.77 (d, J 8.9, 1H), 5.83 (s, 1H), 2.71-2.61 (m, 1H), 1.91-1.81 (m, 1H), 0.95-0.82 (m, 4H), 0.70-0.55 (m, 4H). MS (m/z): 346.27 [M-2HCl]−.

Workup

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

Sources & evidence

ORD record
ord-6a908f81adc948b381d9e1b2a4e94e11
Source dataset
uspto-grants-2013_02
Patent number
US08377970B2

Reaction notes

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