Hydrochloric Acid → HCID 67114935, compound

HRID 1408536Notes

Reaction equation

HRID 1408536 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:28])[C:20]4[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:21]=4[F:27])=[CH:14][CH:13]=3)[N:5]=2)[CH2:3][CH2:2]1.FC1C=CC=C(F)C=1C(O)=O.[ClH:40]>C1COCC1.C(OCC)C>[ClH:40].[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:28])[C:20]4[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:21]=4[F:27])=[CH:14][CH:13]=3)[N:5]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 97962,6-Difluorobenzoic acidHCID 51352974HCID 51352974, compound

Product 1

HCID 67114935HCID 67114935, 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]-2,6-difluorobenzamide (71 mg) was prepared from 2,6-difluorobenzoic acid (126 mg, 0.799 mmol) and intermediate 30 (120 mg, 0.5 mmol) as a brown 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 (69 mg) as a brown solid. M.P. 196-201° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 11.16 (s, 1H), 8.72 (d, J 2.3, 1H), 8.26 (dd, J 2.5, 8.9, 1H), 7.75 (d, J 8.8, 1H), 7.65-7.60 (m, 1H), 7.27 (t, J 8.0, 2H), 5.82 (s, 1H), 2.69-2.60 (m, 1H), 1.90-1.82 (m, 1H), 0.94-0.82 (m, 4H), 0.70-0.59 (m, 4H). MS (m/z): [M+H−HCl]+.

Workup

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

Sources & evidence

ORD record
ord-2e78d1ce224c44809dc096a4cd157fb1
Source dataset
uspto-grants-2014_12
Patent number
US08921364B2

Reaction notes

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