Hydrochloric Acid → HCID 67199279, compound

HRID 388828Notes

Reaction equation

HRID 388828 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:27])[CH2:20][C:21]4[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=4)=[CH:14][CH:13]=3)[N:5]=2)[CH2:3][CH2:2]1.N1C=CC(CC(O)=O)=CC=1.[ClH:38]>C(OCC)C>[ClH:38].[CH:1]1([C:4]2[CH:8]=[C:7]([CH:9]3[CH2:10][CH2:11]3)[N:6]([C:12]3[CH:13]=[CH:14][C:15]([NH:18][C:19](=[O:27])[CH2:20][C:21]4[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=4)=[CH:16][CH:17]=3)[N:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 342284-Pyridineacetic acidHCID 51352794HCID 51352794, compound

Product 1

HCID 67199279HCID 67199279, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Following the general procedure-1, N-[4-(3,5-dicyclopropyl-1H-pyrazol-1-yl)phenyl]-2-(pyridin-4-yl)acetamide (89 mg) was prepared from 2-(pyridin-4-yl)acetic acid (104 mg, 0.60 mmol) and intermediate 27 (120 mg, 0.50 mmol) as an off-white solid. This amide was dissolved in saturated HCl in diethyl ether at 0° C. and stirred for 15 min Solid that separated out was filtered and dried to give the title compound (12 mg). M.P. 175-181° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 10.75 (s, 1H), 8.86 (d, J 6.2, 2H), 8.04 (d, J 5.8, 2H), 7.71 (d, J 8.8, 2H), 7.51 (d, J 8.8, 2H), 5.78 (s, 1H), 4.12 (s, 2H), 1.84-1.72 (m, 2H), 0.91-0.80 (m, 4H), 0.66-0.60 (m, 4H). MS (m/z): 393.09 [M−H]−.

Workup

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

Sources & evidence

ORD record
ord-2736dd3c691d4d1cbfe458d439cae09a
Source dataset
uspto-grants-2013_02
Patent number
US08377970B2

Reaction notes

Loading…