Hydrochloric Acid → HCID 52913842, compound

HRID 881055Notes

Reaction equation

HRID 881055 reaction equation
[CH:1]1([C:4]2[N:8]([C:9]3[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:29])[CH:17]([C:19]4[CH:20]=[C:21]5[C:26](=[CH:27][CH:28]=4)[N:25]=[CH:24][CH:23]=[CH:22]5)[CH3:18])=[CH:11][CH:10]=3)[N:7]=[C:6]([C:30]([F:33])([F:32])[F:31])[CH:5]=2)[CH2:3][CH2:2]1.[ClH:34]>C1COCC1.C(OCC)C>[ClH:34].[CH:1]1([C:4]2[N:8]([C:9]3[CH:10]=[CH:11][C:12]([NH:15][C:16](=[O:29])[CH:17]([C:19]4[CH:20]=[C:21]5[C:26](=[CH:27][CH:28]=4)[N:25]=[CH:24][CH:23]=[CH:22]5)[CH3:18])=[CH:13][CH:14]=3)[N:7]=[C:6]([C:30]([F:32])([F:31])[F:33])[CH:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 52913843HCID 52913843, compound

Product 1

HCID 52913842HCID 52913842, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure-1, N-{4-[5-cyclopropyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl}-2-(quinolin-6-yl)propanamide (74 mg) was prepared from intermediate 15 (150 mg, 0.56 mmol) and intermediate 38 (180 mg, 0.89 mmol) as a brown 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 (45 mg) as a brown solid. M. P.: 168-170° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 10.61 (s, 1H), 9.11 (d, J 3.7, 1H), 8.87 (d, J 8, 1H), 8.18 (d, J 9, 2H), 8.07 (dd, J 1.6, 8.8, 1H), 7.85 (dd, J 4.9, 8.3, 1H), 7.79 (d, J 8.9, 2H), 7.55 (d, J 8.9, 2H), 6.59 (s, 1H), 4.20 (q, J 6.8, 1H), 1.80-1.70 (m, 1H), 1.57 (d, J 6.8, 3H), 1.00-0.90 (m, 2H), 0.80-0.70 (m, 2H). MS (m/z): 451.11 [M+H−HCl]−.

Workup

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

Sources & evidence

ORD record
ord-1e9d9ab53d994c50a8a2ac54b62ae05e
Source dataset
uspto-grants-2015_03
Patent number
US08993612B2

Reaction notes

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