Hydrochloric Acid → HCID 67114996, compound

HRID 388831Notes

Reaction equation

HRID 388831 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[S:25][CH:24]=[N:23][C:22]=4[CH3:26])=[O:20])=[CH:14][CH:13]=3)[N:5]=2)[CH2:3][CH2:2]1.CC1N=CSC=1C(O)=O.[ClH:36]>C1COCC1.C(OCC)C>[ClH:36].[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[S:25][CH:24]=[N:23][C:22]=4[CH3:26])=[O:20])=[CH:14][CH:13]=3)[N:5]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2098054-Methylthiazole-5-carboxylic acidHCID 51352975N-[6-(3,5-dicyclopropyl-1H-pyrazol-1-yl)pyridin-3-yl]-4-methylthiazole-5-carboxamide

Product 1

HCID 67114996HCID 67114996, 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]-4-methylthiazole-5-carboxamide (55 mg) was prepared from 4-methylthiazole-5-carboxylic acid (130 mg, 0.83 mmol) and intermediate 30 (200 mg, 0.83 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 (50 mg) as an off-white solid. M.P. 93-98° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 10.57 (s, 1H), 9.16 (s, 1H), 8.74 (s, 1H), 8.23 (dd, J 2.4, 8.9, 1H), 7.73 (d, J 8.9, 1H), 5.82 (s, 1H), 2.70-2.60 (m, 4H), 1.88-1.80 (m, 1H), 0.93-0.81 (m, 4H), 0.69-0.58 (m, 4H). MS (m/z): 366.36 [M+H—HCl]+.

Workup

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

Sources & evidence

ORD record
ord-63414fd9a0684468b69ad9d183e7ff11
Source dataset
uspto-grants-2013_02
Patent number
US08377970B2

Reaction notes

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