Hydrochloric Acid → HCID 67199442, compound

HRID 1408533Notes

Reaction equation

HRID 1408533 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][C:13]=3[F:27])[N:5]=2)[CH2:3][CH2:2]1.C(O)(=O)C1C=CC=NC=1.[ClH:37]>C1COCC1.C(OCC)C>[ClH:37].[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][C:13]=3[F:27])[N:5]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 938Nicotinic AcidHCID 51352976HCID 51352976, compound

Product 1

HCID 67199442HCID 67199442, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure-1, N-[4-(3,5-dicyclopropyl-1H-pyrazol-1-yl)-3-fluorophenyl]nicotinamide (130 mg) was prepared from intermediate 28 (200 mg, 0.78 mmol) and nicotinic acid (153 mg, 1.2 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 (70 mg) as a white solid. M.P.: 201.2-203.4° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 11.04 (s, 1H), 9.26 (s, 1H), 8.87 (d, J 4.8, 1H), 8.58 (d, J 4.8, 1H), 7.97 (d, J 12.8, 1H), 7.81 (d, J 5, 1H), 7.71 (d, J 8.6, 1H), 7.52 (t, J 8.7, 1H), 5.76 (s, 1H), 1.90-1.80 (m, 1H), 1.58-1.48 (m, 1H), 0.90-0.78 (m, 4H), 0.65-0.55 (m, 4H). MS (m/z): 363.14 [M+H−HCl]+.

Workup

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

Sources & evidence

ORD record
ord-b8babbebb4fd4066a13feee9805f92d7
Source dataset
uspto-grants-2014_12
Patent number
US08921364B2

Reaction notes

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