3-Chloropropanesulphonyl chloride → HCID 9865957, compound

HRID 367262Notes

Reaction equation

HRID 367262 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].CCN(C(C)C)C(C)C.[Cl:29][CH2:30][CH2:31][CH2:32][S:33](Cl)(=[O:35])=[O:34]>C(Cl)Cl>[CH2:1]([N:5]1[C:10]2=[CH:11][N:12]([S:33]([CH2:32][CH2:31][CH2:30][Cl:29])(=[O:35])=[O:34])[N: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]

Participants

5

Reactant 3

HCID 154103-Chloropropanesulphonyl chlorideHCID 81531DiisopropylethylamineHCID 11076323HCID 11076323, compound

Product 1

HCID 9865957HCID 9865957, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

To 222 mg (0.84 mmol) of 4,6-dibutyl-1,4-dihydro-pyrazolo[4,3-d]pyrimidine-5,7-dione in 10 mL CH2Cl2 was added 0.22 mL (163 mg, 1.26 mmol) of i-Pr2NEt followed by 0.11 mL (164 mg, 0.924 mmol) of 3-chloro-n-propanesulfonyl chloride. The resulting solution was stirred at 23° C. for 16 h after which time TLC shows that all starting material had been consumed. The reaction mixture was poured into brine, extracted with 2×50 mL EtOAc, and the combined organics were washed with 1×50 mL brine, dried over MgSO4, filtered and evaporated to a yellow solid. Flash chromatography on silica gel, eluting with CH2Cl2 /EtOAc (40/1 to 20/1) gave the title compound. Recrystallization from hot hexanes/EtOAc gave 168 mg (0.415 mmol, a 49% yield) of the title compound as a white crystalline solid. mp: 67-68° C.; 1H NMR (300 MHz, CDCl3); δ 0.92-1.02 (m, 6H), 1.34-1.49 (m, 4H), 1.56-1.79 (m, 4H), 2.21-2.34 (m, 2H), 3.65 (t, J=6.1 Hz, 2H), 3.79-3.88 (m, 4H), 4.17 (t, J=7.3 Hz, 2H), 7.87 (s, 1H); IR (KBr, cm-1): 3137w, 2958w, 1718m, 1677s, 1626w, 1380m, 1166m; MS (ES) m/z (relative intensity): 405 (M+ +H, 100); Anal. Calcd. for C16H25ClN4O4S: C, 47.46; H, 6.22, N, 13.84. Found: C, 46.80; H, 6.06; N, 13.24.

Workup

  1. customhad been consumed
  2. additionThe reaction mixture was poured into brine
  3. extractionextracted with 2×50 mL EtOAc
  4. washthe combined organics were washed with 1×50 mL brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated to a yellow solid
  8. washFlash chromatography on silica gel, eluting with CH2Cl2 /EtOAc (40/1 to 20/1)

Sources & evidence

ORD record
ord-2372eb053bb646b1922afcb229a91fab
Source dataset
uspto-grants-2000_10
Patent number
US06133273

Reaction notes

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