Dimethylformamide → HCID 86683413, compound

HRID 579436Notes

Reaction equation

HRID 579436 reaction equation
Br[C:2]1[S:3][C:4]([C:7]([N:9]2[CH2:18][CH2:17][C:16]3[C:15]([CH:19]=[O:20])=[C:14]([O:21][CH3:22])[CH:13]=[CH:12][C:11]=3[CH2:10]2)=[O:8])=[CH:5][N:6]=1.CN(C)C=O.[CH3:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:22][O:21][C:14]1[CH:13]=[CH:12][C:11]2[CH2:10][N:9]([C:7]([C:4]3[S:3][C:2]([N:32]4[CH2:33][CH2:34][N:29]([CH3:28])[CH2:30][CH2:31]4)=[N:6][CH:5]=3)=[O:8])[CH2:18][CH2:17][C:16]=2[C:15]=1[CH:19]=[O:20]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 86683412HCID 86683412, compound

Product 1

HCID 86683413HCID 86683413, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-(2-Bromo-thiazole-5-carbonyl)-6-methoxy-1,2,3,4-tetrahydro-isoquinoline-5-carbaldehyde (229 mg, 0.60 mg) in abs. N,N-dimethylformamide (4 mL), N-methyl piperazine (133 μL, 120 mg, 1.20 mmol) and dry potassium carbonate (248 mg, 1.80 mmol) was added. The resultant mixture was stirred under nitrogen at 100° C. for 2 h in a closed vial. The reaction was cooled, water (10 mL) was added, and the resultant solution was extracted with ethyl acetate (3×15 mL) The combined organic layers were dried (MgSO4) and evaporated to afford title compound (92 mg, 0.23 mmol, 38%) as a pale yellow crystalline solid.

Workup

  1. temperatureThe reaction was cooled
  2. extractionthe resultant solution was extracted with ethyl acetate (3×15 mL) The combined organic layers
  3. dry with materialwere dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-5f7b29ead3114c228b6617fe5e1d4d06
Source dataset
uspto-grants-2015_05
Patent number
US09040714B2

Reaction notes

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