Hydrochloric Acid → HCID 52914065, compound

HRID 881056Notes

Reaction equation

HRID 881056 reaction equation
[CH:1]1([C:4]2[N:8]([C:9]3[N:14]=[CH:13][C:12]([NH:15][C:16](=[O:28])[CH2:17][C:18]4[CH:19]=[C:20]5[C:25](=[CH:26][CH:27]=4)[N:24]=[CH:23][CH:22]=[CH:21]5)=[CH:11][CH:10]=3)[N:7]=[C:6]([C:29]([F:32])([F:31])[F:30])[CH:5]=2)[CH2:3][CH2:2]1.[ClH:33]>C1COCC1.C(OCC)C>[ClH:33].[CH:1]1([C:4]2[N:8]([C:9]3[N:14]=[CH:13][C:12]([NH:15][C:16](=[O:28])[CH2:17][C:18]4[CH:19]=[C:20]5[C:25](=[CH:26][CH:27]=4)[N:24]=[CH:23][CH:22]=[CH:21]5)=[CH:11][CH:10]=3)[N:7]=[C:6]([C:29]([F:30])([F:32])[F:31])[CH:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 52914066HCID 52914066, compound

Product 1

HCID 52914065HCID 52914065, 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-(quinolin-6-yl)acetamide (67 mg) was prepared from intermediate 30 (133 mg, 0.71 mmol) and intermediate 17 (120 mg, 0.45 mmol) as a pale yellow 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 (63 mg) as a white solid. M. P. 225-230° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 10.96 (s, 1H), 9.15 (d, J 4.4, 1H), 8.90 (d, J 8.0, 1H), 8.80 (d, J 2.3, 1H), 8.30 (dd, J 2.4, 8.8, 1H), 8.21 (d, J 8.7, 1H), 8.18 (s, 1H), 8.03 (d, J 8.3, 1H), 7.90 (dd, J 5, 8.2, 1H), 7.75 (d, J 8.8, 1H), 6.61 (s, 1H), 4.06 (s, 2H), 2.51-2.40 (m, 1H), 1.01-0.90 (m, 2H), 0.81-0.70 (m, 2H). MS (m/z): 436.02 [M−H−2HCl]−.

Workup

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

Sources & evidence

ORD record
ord-7d4a34772ebb40a9b0ed36236170899e
Source dataset
uspto-grants-2015_03
Patent number
US08993612B2

Reaction notes

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