1-Propanesulfonyl chloride → HCID 23287917, compound

HRID 367263Notes

Reaction equation

HRID 367263 reaction equation
[CH2:1]([N:5]1[C:10]2[CH:11]=[N:12][NH:13][C:9]=2[C:8](=[O:14])[N:7]([CH2:15][CH2:16][CH2:17][CH3:18])[C:6]1=[O:19])[CH2:2][CH2:3][CH3:4].[CH2:20]([S:23](Cl)(=[O:25])=[O:24])[CH2:21][CH3:22].C(Cl)Cl.CCOC(C)=O>C(Cl)Cl>[CH2:1]([N:5]1[C:10]2[CH:11]=[N:12][N:13]([S:23]([CH2:20][CH2:21][CH3:22])(=[O:25])=[O:24])[C:9]=2[C:8](=[O:14])[N:7]([CH2:15][CH2:16][CH2:17][CH3:18])[C:6]1=[O:19])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 662791-Propanesulfonyl chlorideHCID 11076323HCID 11076323, compoundHCID 21226138Dichloromethane ethylacetate

Product 1

HCID 23287917HCID 23287917, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

To 500 mg (2.6-2.8 mmol/g resin) of piperidinomethyl polystyrene resin in 25 mL CH2Cl2 was added 280 mg (1.06 mmol) of 4,6-dibutyl-1,4-dihydro-pyrazolo[4,3-d]pyrimidine-5,7-dione followed by 166 mg (1.17 mmol) of propanesulfonyl chloride. The resulting solution was stirred at 23° C. for 3 h after which time TLC showed that all starting material (4/1 CH2Cl2 /EtOAc; Rf =0.15) had been consumed. The reaction mixture was filtered, the filtered cake washed with 3×5 mL CH2Cl2, and the combined organics were evaporated to give crude yellow oil. Flash chromatography on silica gel, eluting with CH2Cl2 /EtOAc (40/1 to 10/1) gave 359 mg (0.97 mmol, a 92% yield) of the title compound as a yellow solid. mp: 44-48° C.; 1H NMR (300 MHz, CDCl3); δ 0.93-1.17 (m, 9H), 1.35-1.44 (m, 4H), 1.61-1.83 (m, 4H), 2.06-2.33 (m, 2H), 3.51-3.68 (m, 2H), 3.85 (t, J=7.5 Hz, 2H), 4.02 (t, J=7.4 Hz, 2H), 7.88 (s, 1H); IR (KBr, cm-1): 3231w, 2960m, 1719m, 1675s, 1620m, 1387m, 1289m, 1171m, 1066m; MS (ES) m/z (relative intensity): 371 (M+ +H, 100). Anal. Calcd. for C16H26N4O4S: C, 51.87; H, 7.07, N, 15.12. Found: C, 46.22; H, 6.65; N, 11.91

Workup

  1. customhad been consumed
  2. filtrationThe reaction mixture was filtered
  3. washthe filtered cake washed with 3×5 mL CH2Cl2
  4. customthe combined organics were evaporated
  5. customto give crude yellow oil
  6. washFlash chromatography on silica gel, eluting with CH2Cl2 /EtOAc (40/1 to 10/1)
  7. customgave 359 mg (0.97 mmol

Sources & evidence

ORD record
ord-8f1636ebed5f47e0994264c57587c1e8
Source dataset
uspto-grants-2000_10
Patent number
US06133273

Reaction notes

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