Hydrochloric Acid → HCID 67198415, compound

HRID 388847Notes

Reaction equation

HRID 388847 reaction equation
[CH:1]1([C:4]2[N:8]([C:9]3[N:14]=[CH:13][C:12]([NH:15][C:16](=[O:24])[CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=4)=[CH:11][CH:10]=3)[N:7]=[C:6]([C:25]([F:28])([F:27])[F:26])[CH:5]=2)[CH2:3][CH2:2]1.N1C=CC=CC=1CC(O)=O.[ClH:39]>C1COCC1.C(OCC)C>[ClH:39].[CH:1]1([C:4]2[N:8]([C:9]3[N:14]=[CH:13][C:12]([NH:15][C:16](=[O:24])[CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=4)=[CH:11][CH:10]=3)[N:7]=[C:6]([C:25]([F:28])([F:27])[F:26])[CH:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 853182-Pyridineacetic acidHCID 51353309HCID 51353309, compound

Product 1

HCID 67198415HCID 67198415, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure-1, N-{6-[5-cyclopropyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]pyridin-3-yl}2-(pyridin-2-yl)acetamide (200 mg) was prepared from 2-(pyridin-2-yl)acetic acid (207 mg, 1.2 mmol) and intermediate 36 (200 mg, 0.75 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 (210 mg) as an Off-white solid M.P.: 179-181° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 11.38 (s, 1H), 8.90 (dd, J 0.8, 5.7, 1H), 8.82 (d, J 2.5, 1H), 8.54 (t, J 6.7, 1H) 8.30 (dd, J 2.6, 8.8, 1H), 8.06 (d, J 8, 1H), 7.96 (t, J 6.7, 1H), 7.77 (d, J 8.8, 1H), 6.63 (s, 1H), 4.41 (s, 2H), 2.50-2.41 (m, 1H), 1.00-0.91 (m, 2H), 0.79-0.72 (m, 2H). MS (m/z): 385.60 [M−H—HCl]−.

Workup

  1. customSolid that separated out
  2. filtrationwas filtered
  3. customdried

Sources & evidence

ORD record
ord-cd065ac61c0c4cdb8c88504204e60e28
Source dataset
uspto-grants-2013_02
Patent number
US08377970B2

Reaction notes

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