Hydrochloric Acid → HCID 52913514, compound

HRID 881049Notes

Reaction equation

HRID 881049 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]([C:21]4[CH:22]=[C:23]5[C:28](=[CH:29][CH:30]=4)[N:27]=[CH:26][CH:25]=[CH:24]5)=[O:20])=[CH:14][CH:13]=3)[N:5]=2)[CH2:3][CH2:2]1.[ClH:31]>C1COCC1.C(OCC)C>[ClH:31].[CH:1]1([C:4]2[CH:8]=[C:7]([CH:9]3[CH2:11][CH2:10]3)[N:6]([C:12]3[CH:13]=[CH:14][C:15]([NH:18][C:19]([C:21]4[CH:22]=[C:23]5[C:28](=[CH:29][CH:30]=4)[N:27]=[CH:26][CH:25]=[CH:24]5)=[O:20])=[CH:16][CH:17]=3)[N:5]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 52913515HCID 52913515, compound

Product 1

HCID 52913514HCID 52913514, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure-1, N-[4-(3,5-dicyclopropyl-1H-pyrazol-1-yl)phenyl]quinoline-6-carboxamide (60 mg) was prepared from intermediate 26 (95 mg, 0.55 mmol) and intermediate 12 (120 mg, 0.5 mmol) as a pale yellow solid and dissolved in THF. Saturated HCl in diethyl ether was added at 0° C. to this solution and stirred for 15 min. Solid that separated out was filtered and dried to give the title compound (46 mg) as a white solid. M. P. 114-119° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 11.00 (s, 1H), 9.34 (d, J 3.8, 1H), 9.18 (d, J 8.2, 1H), 9.00 (s, 1H), 8.59 (d, J 8.8, 1H), 8.48 (d, J 8.8, 1H), 8.15-8.05 (m, 1H), 7.61 (d, J 8.9, 2H), 7.61 (d, J 8.9, 2H), 5.84 (s, 1H), 1.89-1.77 (m, 2H), 0.95-0.84 (m, 4H), 0.70-0.64 (m, 4H). MS (m/z): 393.05 [M−H−HCl]−.

Workup

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

Sources & evidence

ORD record
ord-a049a275b5644cc192a8071422f79029
Source dataset
uspto-grants-2015_03
Patent number
US08993612B2

Reaction notes

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