3-Pyridineacetic acid → HCID 67114776, compound

HRID 388839Notes

Reaction equation

HRID 388839 reaction equation
[CH:1]1([C:4]2[N:8]([C:9]3[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:24])[CH2:17][C:18]4[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=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=C(CC(O)=O)C=1.[ClH:39]>C1COCC1.C(OCC)C>[ClH:39].[CH:1]1([C:4]2[N:8]([C:9]3[CH:10]=[CH:11][C:12]([NH:15][C:16](=[O:24])[CH2:17][C:18]4[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=4)=[CH:13][CH:14]=3)[N:7]=[C:6]([C:25]([F:26])([F:27])[F:28])[CH:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 1083-Pyridineacetic acidHCID 313Hydrochloric AcidHCID 67114777HCID 67114777, compound

Product 1

HCID 67114776HCID 67114776, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure-1, N-{-4-[5-cyclopropyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl}-2-(pyridin-3-yl)acetamide (140 mg) was prepared from 3-pyridylacetic acid (124 mg, 0.714 mmol) and intermediate 31 (120 mg, 0.45 mmol) as a 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 (101 mg) as a pale yellow solid. M.P. 196-201° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 10.81 (s, 1H), 8.89 (s, 1H), 8.81 (d, J 5.4, 1H), 8.48 (d, J 7.4, 1H) 8.00-7.97 (m, 1H), 7.80 (d, J 8.7, 2H), 7.58 (d, J 8.7, 2H), 6.59 (s, 1H), 4.04 (s, 2H), 1.84-1.75 (m, 1H), 0.97-0.91 (m, 2H), 0.80-0.75 (m, 2H). MS (m/z): 423.2 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-34c96f769ee440b9a23897a3f1e042c9
Source dataset
uspto-grants-2013_02
Patent number
US08377970B2

Reaction notes

Loading…