4-Methylmorpholine → 4-{2-[4-(tert-Butoxycarbonyl)piperazin-1-yl]-1,3-thiazol-4-yl}benzoic acid

HRID 606568Notes

Reaction equation

HRID 606568 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[S:16])[NH2:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:18][C:19]([C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=1)=O.CN1CCOCC1>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[S:16][CH:18]=[C:19]([C:21]3[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=3)[N:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 27568364-(2-bromoacetyl)benzoic AcidHCID 12093220tert-Butyl 4-carbamothioylpiperazine-1-carboxylate

Product 1

HCID 181867194-{2-[4-(tert-Butoxycarbonyl)piperazin-1-yl]-1,3-thiazol-4-yl}benzoic acidYield 75.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 4-thiocarbamoyl-piperazine-1-carboxylic acid tert-butyl ester (13.3 mmol) in ethanol (60 ml) was added 4-(2-bromoacetyl)-benzoic acid (13.3 mmol) and 4-methylmorpholine (13.9 mmol). The reaction was heated at reflux for 2.5 h. The reaction was concentrated in vacuo and the solid washed with water (200 ml) to yield the title compound as a white solid (3.9 g). 1H NMR (400 MHz, CDCl3) 1.45 (9H, s), 3.58 (8H, m), 4.86 (1H, s), 6.95 (1H,s), 7.97 (2H, d, J 8 Hz), 8.1 (2H, d, J 8 Hz).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 2.5 h
  3. concentrationThe reaction was concentrated in vacuo
  4. washthe solid washed with water (200 ml)

Sources & evidence

ORD record
ord-5e2255d370e94ae9bc60b5b8641d5353
Source dataset
uspto-grants-2011_03
Patent number
US07915300B2

Reaction notes

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