Cyclopentanone → HCID 11260646, compound

HRID 915855Notes

Reaction equation

HRID 915855 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[Cl:31])[N:11]=[C:12]3[C:17]([N:18]4[CH2:23][CH:22]5[CH2:24][CH:19]4[CH2:20][NH:21]5)=[N:16][CH:15]=[N:14][C:13]=23)=[CH:5][CH:4]=1.[Cl-].C([NH+](CC)CC)C.C(N(CC)CC)C.[C:47]1(=O)[CH2:51][CH2:50][CH2:49][CH2:48]1.[BH4-]>C(O)C>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[Cl:31])[N:11]=[C:12]3[C:17]([N:18]4[CH2:23][CH:22]5[CH2:24][CH:19]4[CH2:20][N:21]5[CH:47]4[CH2:51][CH2:50][CH2:49][CH2:48]4)=[N:16][CH:15]=[N:14][C:13]=23)=[CH:5][CH:4]=1

Participants

7

Reactant 5

HCID 8452CyclopentanoneHCID 8471TriethylamineHCID 28123BorohydrideHCID 12698378Triethylazanium chlorideHCID 69430048HCID 69430048, compound

Product 1

HCID 11260646HCID 11260646, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the mixture of Rac-(S,S)-3-(4-chlorophenyl)-2-(2-chlorophenyl)-7-(2,5-diazabicyclo[2.2.1]hept-2-yl)-2H-pyrazolo[4,3-d]pyrimidine HCl salt 4A-1 (50.5 mg, 0.1 mmol), triethylammonium chloride (27 mg, 0.2 mmol), and triethylamine (0.028 ml, 0.2 mmol) in absolute ethanol (1 ml) was added cyclopentanone (8.8 ml, 0.1 mmol), followed by borohydride resin (40 mg, 2.5 mmol/g). The mixture was stirred overnight at room temperature. After removal of solvent and resin, the residue was further purified by HPLC to give Rac-(S,S)-3-(4-chlorophenyl)-2-(2-chlorophenyl)-7-(5-cyclopentyl-2,5-diazabicyclo[2.2.1]hept-2-yl)-2H-pyrazolo[4,3-d]pyrimidine 5A-1 (23 mg, 46%): MS: 504.8 (M+1)+; 1H NMR (400 MHz, CD3OD) δ 8.3 (s, 1H), 8.2 (s, 1H), 7.6 (m, 4H), 7.4 (m, 3H), 6.1 (s, 0.5H), 5.4 (s, 0.5H), 4.6 (m, 1.5H), 4.3 (m, 0.5H), 4.1 (m, 1H), 3.7 (m, 3H), 2.4 (m, 2H), 2.3 (m, 1H), 2.2 (m, 1H), 1.8 (m, 2H), 1.6 (m, 4H).

Workup

  1. customAfter removal of solvent and resin
  2. customthe residue was further purified by HPLC

Sources & evidence

ORD record
ord-f74e780dd32a44698ce5fd0efd0d4519
Source dataset
uspto-grants-2007_09
Patent number
US07268133B2

Reaction notes

Loading…