Hydrochloric Acid → HCID 67200563, compound

HRID 1408534Notes

Reaction equation

HRID 1408534 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][N:23]=[CH:22][CH:21]=4)=[CH:14][C:13]=3[F:27])[N:5]=2)[CH2:3][CH2:2]1.C(O)(=O)C1C=CN=CC=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][N:23]=[CH: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 5922Isonicotinic AcidHCID 51352909HCID 51352909, compound

Product 1

HCID 67200563HCID 67200563, 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]isonicotinamide (107 mg) was prepared from intermediate 28 (200 mg, 0.78 mmol) and isonicotinic acid (153 mg, 1.2 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 (70 mg) as a pale-yellow solid. M.P.: 201.2-203.4° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 10.83 (s, 1H), 8.81 (d, J 5.9, 2H), 7.94 (dd, J 1.9, 12.6, 1H), 7.87 (d, J 5.9, 2H), 7.67 (dd, J 1.4, 8.6, 1H), 7.51 (t, J 8.7, 1H), 5.76 (s, 1H), 1.88-1.78 (m, 1H), 1.58-1.48 (m, 1H), 0.88-0.78 (m, 4H), 0.62-0.50 (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-317e99c07d0246f083d7f27223fe21d7
Source dataset
uspto-grants-2014_12
Patent number
US08921364B2

Reaction notes

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