Acetic Acid → HCID 67204255, compound

HRID 1626320Notes

Reaction equation

HRID 1626320 reaction equation
[C:1]1([C:7]2[N:8]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:9]3[C:14]([N:15]=2)=[C:13]([NH:16][CH2:17][CH2:18][CH:19]=O)[N:12]=[CH:11][N:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[Cl:28][C:29]1[C:34]([Cl:35])=[CH:33][CH:32]=[CH:31][C:30]=1[N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(=O)C>ClCCCl>[Cl:28][C:29]1[C:34]([Cl:35])=[CH:33][CH:32]=[CH:31][C:30]=1[N:36]1[CH2:41][CH2:40][N:39]([CH2:19][CH2:18][CH2:17][NH:16][C:13]2[N:12]=[CH:11][N:10]=[C:9]3[C:14]=2[N:15]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]3[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:38][CH2:37]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 116303721-(2,3-Dichlorophenyl)piperazine hydrochlorideHCID 86670633HCID 86670633, compound

Product 1

HCID 67204255HCID 67204255, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
45 °C

Procedure

To the solution of 3-(8,9-diphenyl-9H-purin-6-ylamino)propanal obtained in step 2 (0.73 g, 2.13 mmol) and 1-(2,3-dichlorophenyl)piperazine hydrochloride (0.6 g, 2.13 mmol) in 1.2-dichloroethane was added Na(OAc)3BH (0.72 g, 3.40 mmol) and acetic acid (0.24 mL, 4.25 mmol) at room temperature and stirred for 18 hours at 45° C. The resulting reaction mixture was concentrated under reduced pressure. The residue was diluted with CH2Cl2, and washed with water. The organic layer thus separated was dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude product thus obtained was purified by preparative HPLC (purification system, Gilson) to provide the title compound (460 mg) as a white solid.

Workup

  1. customThe resulting reaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. additionThe residue was diluted with CH2Cl2
  4. washwashed with water
  5. customThe organic layer thus separated
  6. dry with materialwas dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product thus obtained
  10. customwas purified by preparative HPLC (purification system, Gilson)

Sources & evidence

ORD record
ord-40f8f622f1944acdb93b900064ab3ddd
Source dataset
uspto-grants-2014_07
Patent number
US08785453B2

Reaction notes

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