Hydrochloric Acid → HCID 52913846, compound

HRID 881051Notes

Reaction equation

HRID 881051 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](=[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][C:13]=3[F:32])[N:5]=2)[CH2:3][CH2:2]1.[ClH:33]>C1COCC1.C(OCC)C>[ClH:33].[CH:1]1([C:4]2[CH:8]=[C:7]([CH:9]3[CH2:10][CH2:11]3)[N:6]([C:12]3[CH: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][C:13]=3[F:32])[N:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 52913847HCID 52913847, compound

Product 1

HCID 52913846HCID 52913846, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure-1, N-[4-(3,5-dicyclopropyl-1H-pyrazol-1-yl)-3-fluorophenyl]-2-(quinolin-6-yl)acetamide (95 mg) was prepared from intermediate 13 (200 mg, 0.78 mmol) and intermediate 30 (232 mg, 1.2 mmol) as an 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 (50 mg) as an yellow solid. M. P.: 106.8-108.2° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 10.99 (s, 1H), 9.24 (d, J 4.5, 1H), 9.09 (d, J 8.0, 1H), 8.32-8.25 (m, 2H), 8.12 (d, J 8.6, 1H), 8.05-8.01 (m, 1H), 7.83 (d, J 11.3, 1H), 7.50-7.41 (m, 2H), 5.73 (s, 1H), 4.07 (s, 2H), 1.84-1.76 (m, 1H), 1.52-1.42 (m, 1H), 0.82-0.74 (m, 4H), 0.62-0.52 (m, 4H). MS (m/z): 427.10 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-a2f596b436df4351b4d8262a0a01f0a6
Source dataset
uspto-grants-2015_03
Patent number
US08993612B2

Reaction notes

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