Hydrochloric Acid → HCID 52913958, compound

HRID 881053Notes

Reaction equation

HRID 881053 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](=[O:31])[CH2:20][C:21]4[CH:22]=[C:23]5[C:28](=[CH:29][CH:30]=4)[N:27]=[CH:26][CH:25]=[CH:24]5)=[CH:14][CH:13]=3)[N:5]=2)[CH2:3][CH2:2]1.[ClH:32]>C1COCC1.C(OCC)C>[ClH:32].[ClH:32].[CH:1]1([C:4]2[CH:8]=[C:7]([CH:9]3[CH2:10][CH2:11]3)[N:6]([C:12]3[N:17]=[CH:16][C:15]([NH:18][C:19](=[O:31])[CH2:20][C:21]4[CH:22]=[C:23]5[C:28](=[CH:29][CH:30]=4)[N:27]=[CH:26][CH:25]=[CH:24]5)=[CH:14][CH:13]=3)[N:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 52913959HCID 52913959, compound

Product 1

HCID 52913958HCID 52913958, 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]-2-(quinolin-6-yl)acetamide (138 mg) was prepared from intermediate 30 (112 mg, 0.59 mmol) and intermediate 14 (120 mg, 0.49 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 (34 mg) as an off-white solid. M. P. 62-67° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 10.86 (s, 1H), 9.21 (d, J 4.4, 1H), 9.04 (d, J 8.1, 1H), 8.69 (s, 1H), 8.30-8.22 (m, 2H), 8.18 (d, J 8.1, 1H), 8.09 (d, J 8.4, 1H), 8.00-7.97 (m, 1H), 7.68 (d, J 8.8, 1H), 5.80 (s, 1H), 4.05 (s, 2H), 2.69-2.55 (m, 1H), 1.89-1.75 (m, 1H), 0.97-0.78 (m, 4H), 0.70-0.50 (m, 4H). MS (m/z): 410.26 [M+H−2HCl]+.

Workup

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

Sources & evidence

ORD record
ord-b46b34c36a434779a033abad6391ff2c
Source dataset
uspto-grants-2015_03
Patent number
US08993612B2

Reaction notes

Loading…