Hydrochloric Acid → N-{6-[5-cyclopropyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]pyridin-3-yl}-4-methylthiazole-5-carboxamide hydrochloride

HRID 1408548Notes

Reaction equation

HRID 1408548 reaction equation
[CH:1]1([C:4]2[N:8]([C:9]3[N:14]=[CH:13][C:12]([NH:15][C:16]([C:18]4[S:22][CH:21]=[N:20][C:19]=4[CH3:23])=[O:17])=[CH:11][CH:10]=3)[N:7]=[C:6]([C:24]([F:27])([F:26])[F:25])[CH:5]=2)[CH2:3][CH2:2]1.CC1N=CSC=1C([Cl:36])=O.Cl>C1COCC1.C(OCC)C>[ClH:36].[CH:1]1([C:4]2[N:8]([C:9]3[N:14]=[CH:13][C:12]([NH:15][C:16]([C:18]4[S:22][CH:21]=[N:20][C:19]=4[CH3:23])=[O:17])=[CH:11][CH:10]=3)[N:7]=[C:6]([C:24]([F:26])([F:27])[F:25])[CH:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 124702104-Methyl-1,3-thiazole-5-carbonyl chlorideHCID 57518342N-[6-[5-cyclopropyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]pyridin-3-yl]-4-methylthiazole-5-carboxamide

Product 1

HCID 67114836N-{6-[5-cyclopropyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]pyridin-3-yl}-4-methylthiazole-5-carboxamide hydrochlorideYield 140.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure-2, N-{6-[5-cyclopropyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]pyridin-3-yl}-4-methylthiazole-5-carboxamide (45 mg) was prepared from 4-methylthiazole-5-carbonyl chloride (132 mg, 0.82 mmol) and intermediate 36 (200 mg, 0.75 mmol) as a white 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 (69 mg) as a pale-yellow solid. M.P. 180-183° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 10.68 (s, 1H), 9.18 (s, 1H), 8.85 (d, J 2.4, 1H), 8.35 (dd, J 2.5, 8.8, 1H), 7.79 (d, J 8.8, 1H), 6.64 (s, 1H), 2.64 (s, 3H), 2.51-2.40 (m, 1H), 1.10-0.95 (m, 2H), 0.81-0.74 (m, 2H). MS (m/z): 394.23 [M+H]+.

Workup

  1. customthat separated out
  2. filtrationwas filtered
  3. customdried

Sources & evidence

ORD record
ord-e2eecfc4382049e3b757acc97f3e8060
Source dataset
uspto-grants-2014_12
Patent number
US08921364B2

Reaction notes

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