Dimethylformamide → HCID 58609904, compound

HRID 408501Notes

Reaction equation

HRID 408501 reaction equation
Br[C:2]1[S:6][C:5]([NH:7][C:8]([C:10]2([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH2:12][CH2:11]2)=[O:9])=[N:4][CH:3]=1.[NH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.CN(C)C=[O:30]>>[N:21]1([C:2]2[S:6][C:5]([NH:7][C:8]([C:10]3([C:13]4[CH:18]=[CH:17][C:16]5[O:19][CH2:20][O:30][C:15]=5[CH:14]=4)[CH2:12][CH2:11]3)=[O:9])=[N:4][CH:3]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 8082PiperidineHCID 58609889HCID 58609889, compound

Product 1

HCID 58609904HCID 58609904, compoundYield 2.96%

Procedure

1-(4-Methoxy-phenyl)-cyclopropanecarboxylic acid (5-bromo-thiazol-2-yl)-amide (110.4 mg, 0.3125 mmol) was dissolved in 3 mL of N,N-dimethylformamide containing piperidine (148.2 μL, 1.500 mmol). The reaction mixture was placed in a sealed tube and subjected to microwave irradiation for 5 minutes at 100° C. The resulting crude product was purified by reverse-phase preparative liquid chromatography to give the pure product (3.44 mg, 0.00926 mmol, 2.96%) ESI-MS m/z calc. 371.1. found; 372.3 (M+1)+ Retention time 3.29 minutes.

Workup

  1. customThe reaction mixture was placed in a sealed tube
  2. customirradiation for 5 minutes at 100° C
  3. customThe resulting crude product was purified by reverse-phase preparative liquid chromatography

Sources & evidence

ORD record
ord-190d820c097445f78da364cdf8c0fe95
Source dataset
uspto-grants-2014_06
Patent number
US08759335B2

Reaction notes

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