Water → HCID 59579874, compound

HRID 2279658Notes

Reaction equation

HRID 2279658 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2([CH2:13][NH:14][C:15]([C:17]3[S:21][C:20](Br)=[N:19][C:18]=3[C:23]([F:26])([F:25])[F:24])=[O:16])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:2]=1.[CH3:27][N:28]([CH3:34])[C@@H:29]1[CH2:33][CH2:32][NH:31][CH2:30]1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2([CH2:13][NH:14][C:15]([C:17]3[S:21][C:20]([N:31]4[CH2:32][CH2:33][C@@H:29]([N:28]([CH3:34])[CH3:27])[CH2:30]4)=[N:19][C:18]=3[C:23]([F:26])([F:25])[F:24])=[O:16])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2758521(3R)-(+)-3-(Dimethylamino)pyrrolidineHCID 59579827HCID 59579827, compound

Product 1

HCID 59579874HCID 59579874, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-bromo-4-trifluoromethyl-thiazole-5-carboxylic acid (1-pyridin-3-yl-cyclohexylmethyl)-amide (44.8 mg), dimethyl-(R)-pyrrolidin-3-yl-amine (12.6 mg), and potassium carbonate (15.2 mg) in ACN (1 mL) is heated at 80° C. for 1 h. The mixture is cooled, poured into water and extracted with EtOAc. The extract is concentrated in vacuo and the residue is purified by PTLC (silica gel, 5% MeOH in methylene chloride) to give the title compound. MS (M+1)=482.24; RT=1.03 min. *IC50.

Workup

  1. temperatureThe mixture is cooled
  2. extractionextracted with EtOAc
  3. concentrationThe extract is concentrated in vacuo
  4. customthe residue is purified by PTLC (silica gel, 5% MeOH in methylene chloride)

Sources & evidence

ORD record
ord-b7a9c2348666482d9cad2582c5769b23
Source dataset
uspto-grants-2015_09
Patent number
US09133204B2

Reaction notes

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