Acetonitrile → HCID 59993311, compound

HRID 238249Notes

Reaction equation

HRID 238249 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[NH:10][C:9]([CH:13]([N:15]2[CH2:20][CH2:19][N:18]([S:21]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)(=[O:23])=[O:22])[CH2:17][CH2:16]2)[CH3:14])=[N:8][CH:7]=1)=[O:5])[CH3:2].[CH:32]1(I)[CH2:36][CH2:35][CH2:34][CH2:33]1.C(=O)([O-])[O-].[K+].[K+].CC#N>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:11]([O:12][CH:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)=[N:10][C:9]([CH:13]([N:15]2[CH2:20][CH2:19][N:18]([S:21]([C:24]3[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=3)(=[O:23])=[O:22])[CH2:17][CH2:16]2)[CH3:14])=[N:8][CH:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 73784IodocyclopentaneHCID 59993320HCID 59993320, compound

Product 1

HCID 59993311HCID 59993311, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-6-oxo-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester (90 mg, 0.2 mmol), cyclopentyl iodide (46 μL, 0.4 mmol), and potassium carbonate (138 mg, 1 mmol) in DMF (1 mL) was heated to 90° C. for 1 day. The reaction mixture was then filtered and purified by HPLC (in the absence of TFA) to yield the product. 1H NMR (400 MHz, CDCl3) δ 8.91 (s, 1H), 7.68 (d, J=8.8 Hz, 2H), 6.99 (d, J=8.8 Hz, 2H), 5.58 (m, 1H), 4.36 (q, J=7.1 Hz, 2H), 3.89 (s, 3H), 3.84 (m, 1H), 3.04 (m, 4H), 2.73 (m, 4H), 1.83 (m, 8H), 1.40 (m, 6H); HPLC ret. time 2.80 min, 10-99% CH3CN, 5 min run; ESI-MS m/z 519.5 (M+1)+.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. custompurified by HPLC (in the absence of TFA)
  3. customto yield the product

Sources & evidence

ORD record
ord-328605205b614683b205e851d9d30d4d
Source dataset
uspto-grants-2014_02
Patent number
US08642609B2

Reaction notes

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