4-(2-bromoacetyl)benzoic Acid → HCID 18186612, compound

HRID 1357667Notes

Reaction equation

HRID 1357667 reaction equation
[NH:1]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:7][CH2:6]1)[C:2]([NH2:4])=[S:3].Br[CH2:17][C:18]([C:20]1[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=1)=O>C1COCC1.C(OCC)C>[CH2:14]([O:13][C:11]([N:8]1[CH2:9][CH2:10][CH:5]([NH:1][C:2]2[S:3][CH:17]=[C:18]([C:20]3[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[CH:22][CH:21]=3)[N:4]=2)[CH2:6][CH2:7]1)=[O:12])[CH3:15]

Participants

5

Reactant 2

HCID 27568364-(2-bromoacetyl)benzoic AcidHCID 11535967294622-57-4

Product 1

HCID 18186612HCID 18186612, compoundYield 70,161.203%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 4-thioureidopiperidine-1-carboxylate (3.8 g, 0.0164 mol.) and 4-(2-bromoacetyl)benzoic acid (4 g, 0.0164 mmol) in THF (100 mL) was heated at 70° C. for 2 hours, cooled to room temperature and then diluted with diethyl ether. A resulting solid was collected by filtration and washed with diethyl ether to provide 4-[2-(1-ethoxycarbonylpiperidin-4-ylamino)thiazol-4-yl]benzoic acid (4.32 g, 70% yield) as an off white solid. HNMR (dmso-d6): 7.93 (4H, m), 7.27 (1H, s), 4.05 (2H, q), 3.82 (3H, m), 3.04 (2H, m), 2.02 (2H, m), 1.41 (2H, m), 1.18 (3H, t). LC/MS: M+1: 376.

Workup

  1. filtrationA resulting solid was collected by filtration
  2. washwashed with diethyl ether

Sources & evidence

ORD record
ord-e409ceacdd874eb8bb52f066e5f00c24
Source dataset
uspto-grants-2003_07
Patent number
US06593327B2

Reaction notes

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