5-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid → 6-{[4-(2-tert-Butylphenyl)piperazin-1-yl]carbonyl}-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

HRID 534878Notes

Reaction equation

HRID 534878 reaction equation
Cl.Cl.[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)([CH3:6])([CH3:5])[CH3:4].[O:19]=[C:20]1[N:25]2[CH:26]=[CH:27][S:28][C:24]2=[N:23][CH:22]=[C:21]1[C:29](O)=[O:30].Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1>O.CN(C)C=O.C(N(CC)CC)C>[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][N:16]([C:29]([C:21]2[C:20](=[O:19])[N:25]3[CH:26]=[CH:27][S:28][C:24]3=[N:23][CH:22]=2)=[O:30])[CH2:15][CH2:14]1)([CH3:6])([CH3:4])[CH3:5]

Participants

8

Reactant 4

HCID 7623625-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 667511491-(2-Tert-butylphenyl)piperazine dihydrochloride

Product 1

HCID 667927926-{[4-(2-tert-Butylphenyl)piperazin-1-yl]carbonyl}-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-oneYield 47%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 1-(2-tert-butylphenyl)piperazine dihydrochloride obtained in Reference Example 1 (500 mg), 5-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylic acid (371 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (395 mg), 1-hydroxy-1H-benzotriazole monohydrate (315 mg), triethylamine (0.558 mL), and N,N-dimethylformamide (10 mL) was stirred at room temperature for over-night. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to provide the title compound (320 mg, 47%) as a colorless solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a3b021e2f03f4755aa0f630d1df1a1a6
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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