Hydrochloric Acid → HCID 51352904, compound

HRID 388824Notes

Reaction equation

HRID 388824 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][CH:23]=[N: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: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 5922Isonicotinic AcidHCID 51352905HCID 51352905, compound

Product 1

HCID 51352904HCID 51352904, 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]nicotinamide (220 mg) was prepared from intermediate 27 (200 mg, 0.84 mmol) and isonicotinic acid (164 mg, 1.34 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 (190 mg) as an off-white solid. M.P.: 230.2-232.9° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 10.97 (s, 1H), 9.34 (s, 1H), 8.94 (d, J 3.6, 1H), 8.74 (bs, 1H), 7.93 (d, J 8.8, 3H), 7.60 (d, J 8.8, 2H), 5.82 (s, 1H), 1.90-1.74 (m, 2H), 0.95-0.80 (m, 4H), 0.70-0.60 (m, 4H). MS (m/z): 345.15 [M+H—HCl]+.

Workup

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

Sources & evidence

ORD record
ord-ae4d962d7c184877a2871832b348ea4b
Source dataset
uspto-grants-2013_02
Patent number
US08377970B2

Reaction notes

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