Thiophene-3-carboxylic acid → HCID 15434276, compound

HRID 841914Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=O)=[CH:2]1.C(N(CC)CC)C.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][N:21]=[C:20]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[N:19]=1>C(Cl)Cl>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][N:21]=[C:20]([N:24]2[CH2:25][CH2:26][N:27]([C:6]([C:3]3[CH:4]=[CH:5][S:1][CH:2]=3)=[O:8])[CH2:28][CH2:29]2)[N:19]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1.0 g (7.81 mmol) of 3-thienylcarboxylic acid and 1 mL (7.86 mmol) of triethylamine in 30 mL of CH2Cl2 cooled to 0° C. 0.84 g (7.81 mmol) of ethyl chloroformiate are added. The mixture is maintained at 0° C. for 20 minutes and then 1.5 g (7.81 mmol) of 4-methoxy-2-(1-piperazinyl) pyrimidine dissolved in 10 mL of CH2Cl2 are added to the solution. The temperature is allowed to rise to room temperature and the solution continually stirred for 2 hours and the organic phase is washed with H2O, dried over NaSO4 and the solvent evaporated off under reduced pressure. The resulting oil is treated with ethyl ether to yield a solid which is recrystallised from ethanol/H2O to give 0.8 g (2.63 mmol) of 4-methoxy-2-[4-(3-thienylcarbonyl)-1-piperazinyl]pyrimidine. m.p.=90-92° C.

Workup

addition0.84 g (7.81 mmol) of ethyl chloroformiate are added
additionare added to the solution
customto rise to room temperature
washthe organic phase is washed with H2O
dry with materialdried over NaSO4
customthe solvent evaporated off under reduced pressure
additionThe resulting oil is treated with ethyl ether
customto yield a solid which
customis recrystallised from ethanol/H2O

Sources & evidence

ORD record: ord-79c7ccc44e42476d8b7a47ac5e839548
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06372746B1

Reaction notes

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