Diethylamine → HCID 178440278, compound

HRID 1860562Notes

Reaction equation

HRID 1860562 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[C:14]2=[N:15][C:16]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([NH:27][S:28]([CH:31]=[CH2:32])(=[O:30])=[O:29])=[CH:23][CH:22]=3)=[N:17][C:18](=[O:19])[C:13]2=[C:12]([CH:33]([CH3:35])[CH3:34])[NH:11]1.[CH2:36]([NH:38][CH2:39]C)C>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[C:14]2=[N:15][C:16]([CH2:20][C:21]3[CH:22]=[CH:23][C:24]([NH:27][S:28]([CH:31]=[CH:32][N:38]([CH3:39])[CH3:36])(=[O:30])=[O:29])=[CH:25][CH:26]=3)=[N:17][C:18](=[O:19])[C:13]2=[C:12]([CH:33]([CH3:35])[CH3:34])[NH:11]1

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 178477713HCID 178477713, compound

Product 1

HCID 178440278HCID 178440278, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred, solution of 23 mg (0.042 mmol) of 1-(2,4,6-trichlorophenyl)-3-isopropyl-6-(4-(ethenesulfonamido)benzyl)pyrazolo[3,4-d]pyrimidin-4-one in 1 mL of THF was added 1 mL of 2M diethylamine in THF. The solution was stirred 3 h and concentrated under reduced pressure. The product was dissolved in 1 mL of benzene and 0.05 mL of MeOH, frozen, and lyophilized to afford 25 mg (100%) of 1-(2,4,6-trichlorophenyl)-3-isopropyl-6-(4-(2-(dimethylamino)ethenesulfonamido)benzyl)pyrazolo[3,4-d]pyrimidin-4-one as an amorphous white solid. 1H NMR (300 MHz, DMSO) δ 7.96(s, 2H); 7.19(d, 2H, J=8.5 Hz); 7.08(d, 2H, J=8.8 Hz); 3.79(s, 2H); 3.18-3.32(m, 1H); 3.13(t, 2H, J=7.5 Hz); 2.53(t, 2H, J=7.5 Hz); 1.99(s, 6H); 1.28(d, 6H, J=7.0 Hz).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe product was dissolved in 1 mL of benzene
  3. temperature0.05 mL of MeOH, frozen

Sources & evidence

ORD record
ord-3846e4f074ad493ba135fb1ea15c00cb
Source dataset
uspto-grants-2003_03
Patent number
US06531477B1

Reaction notes

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