Hydrochloric Acid → HCID 52913960, compound

HRID 881054Notes

Reaction equation

HRID 881054 reaction equation
[CH:1]1([C:4]2[N:8]([C:9]3[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]4[CH:19]=[C:20]5[C:25](=[CH:26][CH:27]=4)[N:24]=[CH:23][CH:22]=[CH:21]5)=[O:17])=[CH:11][CH:10]=3)[N:7]=[C:6]([C:28]([F:31])([F:30])[F:29])[CH:5]=2)[CH2:3][CH2:2]1.C1COCC1.[ClH:37]>C(OCC)C>[ClH:37].[CH:1]1([C:4]2[N:8]([C:9]3[CH:10]=[CH:11][C:12]([NH:15][C:16]([C:18]4[CH:19]=[C:20]5[C:25](=[CH:26][CH:27]=4)[N:24]=[CH:23][CH:22]=[CH:21]5)=[O:17])=[CH:13][CH:14]=3)[N:7]=[C:6]([C:28]([F:30])([F:29])[F:31])[CH:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 52913961HCID 52913961, compound

Product 1

HCID 52913960HCID 52913960, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Following general procedure-1, N-{4-[5-cyclopropyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl}quinoline-6-carboxamide (35 mg) was prepared from intermediate 26 (85 mg, 0.49 mmol) and intermediate 15 (120 mg, 0.45 mmol) as a brown solid (35 mg) and dissolved THF. Saturated HCl in diethyl ether was added to the solution at 0° C. and stirred for 15 min. Solid that separated out was filtered and dried to give the title compound (30 mg) as an yellow solid. M. P. 188-192° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 10.86 (s, 1H), 9.15 (d, J 4, 1H), 8.80-8.78 (m, 2H), 8.39 (d, J 8.8, 1H), 8.26 (d, J 8.8, 1H), 8.04 (d, J 8.8, 2H), 7.83-7.80 (m, 1H), 7.67 (d, J 8.8, 2H), 6.62 (s, 1H), 1.89-1.84 (m, 1H), 1.00-0.96 (m, 2H), 0.84-0.80 (m, 2H). MS (m/z): 457.16 [M−H]−.

Workup

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

Sources & evidence

ORD record
ord-7f863d36901644ab9b49e6edf3dfa45d
Source dataset
uspto-grants-2015_03
Patent number
US08993612B2

Reaction notes

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