Dimethylformamide → HCID 15670868, compound

HRID 359387Notes

Reaction equation

HRID 359387 reaction equation
C(N([CH2:6][CH3:7])CC)C.Cl[CH2:9][CH:10]([OH:31])[CH2:11][N:12]1[CH2:17][CH2:16][N:15]([CH:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:14][CH2:13]1.[SH:32][C:33]1[N:38]=[CH:37][N:36]=[C:35]2[NH:39][N:40]=[CH:41][C:34]=12.CN([CH:45]=[O:46])C>>[O:46]1[CH:6]([CH2:7][N:39]2[C:35]3=[N:36][CH:37]=[N:38][C:33]([S:32][CH2:9][CH:10]([OH:31])[CH2:11][N:12]4[CH2:17][CH2:16][N:15]([CH:18]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)[C:19]5[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=5)[CH2:14][CH2:13]4)=[C:34]3[CH:41]=[N:40]2)[CH2:45]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 103601754-(3-Chloro-2-hydroxypropyl)-1-diphenylmethylpiperazineHCID 178527891HCID 178527891, compound

Product 1

HCID 15670868HCID 15670868, compound

Procedure

Triethylamine (0.7 mL, 5 mmol) and 1-(1-chloro-2-hydroxy3-propanyl)-4-(diphenylmethyl)piperazine (1.72 g, 5 mmol) was added to 4-mercapto-1H-pyrazolo[3,4-d]pyrimidine (0.78g, 5 mmol) in DMF (10 mL) in portions over a 5 min period. The solution was stirred under nitrogen for 4 days and DMF was removed under vacuum (50° C., 0.5 mmHg). The residue was dissolved in methylene chloride and the solution was washed with water (1×100 mL), saturated brine (1×100 mL) and the organic layer was filtered through celite and evaporated to give a foam (1.47 g). The crude material was eluted through silica gel using 10% methanol: methylene chloride which was extracted with methylene chloride and the organic layer was dried over Na2SO4 and evaporated and dried in vacuo to give the title compound, 0.36 g (13.9%), mp 87°-92° C. 400 MHz 1H NMR (CDCl3) δ: 8.70 (s, 1H), 8.1 (s, 1H), 7.4 (m, 5H), 7.15 (m, 5H), 4.25 (s, 1H), 4.11 (m, 1H), 3.55 (m, 2H), 3.7-2.4 (m, 15H). DCI/MS (M+1) 517.

Workup

  1. customDMF was removed under vacuum (50° C., 0.5 mmHg)
  2. dissolutionThe residue was dissolved in methylene chloride
  3. washthe solution was washed with water (1×100 mL), saturated brine (1×100 mL)
  4. filtrationthe organic layer was filtered through celite
  5. customevaporated

Sources & evidence

ORD record
ord-addea6814e97419c98e987b42765dc16
Source dataset
uspto-grants-1991_03
Patent number
US05001127

Reaction notes

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