Hydrochloric Acid → HCID 67115926, compound

HRID 1408553Notes

Reaction equation

HRID 1408553 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][N:21]=[CH:20][CH: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.[ClH:29]>C1COCC1.C(OCC)C>[ClH:29].[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][N:21]=[CH:20][CH:19]=4)=[CH:11][CH:10]=3)[N:7]=[C:6]([C:25]([F:28])([F:26])[F:27])[CH:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 51353436HCID 51353436, compound

Product 1

HCID 67115926HCID 67115926, 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-4-yl)acetamide (280 mg) was prepared from 4-(pyridin-4-yl)acetic acid (310 mg, 1.78 mmol) and intermediate 36 (300 mg, 1.12 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 (68 mg) as an Off-white solid M.P.: 185.2-188° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 11.26 (s, 1H), 8.87 (d, J 6.6, 2H), 8.81 (d, J 2.5, 1H), 8.30 (dd, J 2.6, 8.8, 1H), 8.06 (d, J 6.6, 2H), 7.76 (d, J 8.8, 1H), 6.62 (s, 1H), 4.19 (s, 2H), 2.52-2.42 (s, 1H), 1.00-0.91 (m, 2H), 0.80-0.72 (m, 2H). MS (m/z): 385.53 [M−H−HCl]−.

Workup

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

Sources & evidence

ORD record
ord-bc103a8bc6e04b9a9d03ebd2e814aef4
Source dataset
uspto-grants-2014_12
Patent number
US08921364B2

Reaction notes

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