Dimethyl Sulfoxide → HCID 14867576, compound

HRID 654600Notes

Reaction equation

HRID 654600 reaction equation
[CH:1]1([N:7]2[CH2:15][C:14]3[C:13](=[O:16])[N:12]4[N:17]=[C:18]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)[CH:19]=[C:11]4[NH:10][C:9]=3[C:8]2=[O:26])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32].C(=O)([O-])[O-].[K+].[K+].CS(C)=O>O>[CH2:34]([O:33][C:31]([CH2:30][CH2:29][CH2:28][N:10]1[C:9]2[C:8](=[O:26])[N:7]([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[CH2:15][C:14]=2[C:13](=[O:16])[N:12]2[N:17]=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:19]=[C:11]12)=[O:32])[CH3:35]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 178515268HCID 178515268, compound

Product 1

HCID 14867576HCID 14867576, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 100 g (2.87) mmole) of 6-cyclohexyl-4,7-dihydro-2-phenyl-5H-pyrazolo[1,5-a]pyrrolo[3,4-d]pyrimidine-5,8-dione (see preparation 1), 0.82 ml. (5.7 mmoles), of ethyl 4-bromobutyrate and 0.41 g., 3.0 mmole of potassium carbonate in 11 ml. of -dimethyl-sulfoxide (DMSO) was stirred at 50° C. for 16.5 hours. Then 35 ml. of water was added and the mixture was suction filtered. The collected solid was washed with more water and air dried. The crude solid was recrystallized from 95% ethanol (100 ml), reflux cooled to room temperature, affording 1.11 g (84% yield) of the titled compound as very fine white needles, m.p. 195°-196° C. 1H NMR (CDCl3, δ) 8.06 (d, 2H, phenyl-H (ortho), 7.45 (m, 3H, phenyl-H), 6.70 (s, 1H, pyrazole-H, 4.74 (t, 2H, J=Hz, 4-NCH 2), 4.37 (s, 2H, lactam CH2), 4.16 (q, 2H, J=7 Hz, OCH2), 4.15 (m, 1H, 6-NCH), 2.49 (t, 2H, CH2CO2C2H5), 2.23 (m, 2H, CH2), 1.15-1.95 (m, 10H, cyclohexyl CH2), 1.26 (t, 3H, J"7 Hz, CH3.

Workup

  1. filtrationfiltered
  2. washThe collected solid was washed with more water and air
  3. customdried
  4. customThe crude solid was recrystallized from 95% ethanol (100 ml)
  5. temperaturereflux

Sources & evidence

ORD record
ord-3b2708b501654ef098fcb6c8675186af
Source dataset
uspto-grants-1992_07
Patent number
US05132424

Reaction notes

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