Hydrochloric Acid → HCID 52913848, compound

HRID 881052Notes

Reaction equation

HRID 881052 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[N: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].[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[N: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)[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 52913849HCID 52913849, compound

Product 1

HCID 52913848HCID 52913848, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure-1, N-[6-(3,5-dicyclopropyl-1H-pyrazol-1-yl)pyridin-3-yl]quinoline-6-carboxamide (71 mg) was prepared from intermediate 26 (103 mg, 0.59 mmol) and intermediate 14 (120 mg, 0.49 mmol) as an orange 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 (62 mg) as an yellow solid. M. P. 232-238° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 11.09 (s, 1H), 9.25 (d, J 4.0, 1H), 9.02 (d, J 7.3, 1H), 8.93 (d, J 8.4, 2H), 8.53 (d, J 9.0, 1H), 8.43-8.36 (m, 2H), 8.02-7.95 (m, 1H), 7.78 (d, J 8.8, 1H), 5.83 (s, 1H), 2.74-2.65 (m, 1H), 1.93-1.84 (m, 1H), 1.00-0.80 (m, 4H), 0.74-0.58 (m, 4H). MS (m/z): 393.94 [M−H−2HCl]−.

Workup

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

Sources & evidence

ORD record
ord-3e062bf43476416c9a19221527a6fb63
Source dataset
uspto-grants-2015_03
Patent number
US08993612B2

Reaction notes

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