Hydrochloric Acid → HCID 86652977, compound

HRID 388842Notes

Reaction equation

HRID 388842 reaction equation
[Cl:1][C:2]1[C:3]([C:27]([F:30])([F:29])[F:28])=[N:4][N:5]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:25])[CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)=[CH:12][C:11]=2[F:26])[C:6]=1[CH:7]1[CH2:9][CH2:8]1.N1C=CC=CC=1CC(O)=O.Cl>C1COCC1.C(OCC)C>[ClH:1].[Cl:1][C:2]1[C:3]([C:27]([F:30])([F:29])[F:28])=[N:4][N:5]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:25])[CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)=[CH:12][C:11]=2[F:26])[C:6]=1[CH:7]1[CH2:9][CH2:8]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 853182-Pyridineacetic acidHCID 67114802HCID 67114802, compound

Product 1

HCID 86652977HCID 86652977, compoundYield 30.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure-1, N-{4-[4-chloro-5-cyclopropyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-3-fluorophenyl}-2-(pyridin-2-yl)acetamide (150 mg) was prepared from 2-(pyridin-2-yl)acetic acid (97 mg, 0.56 mmol) and intermediate 34 (150 mg, 0.47 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 (25 mg) as a white solid. M.P.: 169-171° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 11.03 (s, 1H), 8.75 (d, J 3.9, 1H), 8.29-8.20 (m, 1H), 8.88 (d, J 12.6, 1H), 7.79 (d, J 7.4, 1H), 7.73-7.69 (m, 1H), 7.67 (t, J 8.7, 1H), 7.51 (d, J 8.6, 1H), 4.17 (s, 2H), 1.80-1.70 (m, 1H), 0.90-0.80 (m, 2H), 0.72-0.60 (m, 2H). MS (m/z): 439.15 [M+H—HCl]+.

Workup

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

Sources & evidence

ORD record
ord-0119e31d4bc44e3886094812130caf92
Source dataset
uspto-grants-2013_02
Patent number
US08377970B2

Reaction notes

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