Acetone → HCID 68910000, compound

HRID 729512Notes

Reaction equation

HRID 729512 reaction equation
[CH:1]12[CH2:7][CH:4]([NH:5][CH2:6]1)[CH2:3][N:2]2[C:8]1[N:13]=[C:12]([S:14][CH3:15])[N:11]=[C:10]([C:16]2[CH:21]=[CH:20][N:19]=[C:18]([NH:22][CH:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH3:24])[CH:17]=2)[CH:9]=1.[CH3:31][C:32]([CH3:34])=O.CO>C(Cl)(Cl)Cl.C(Cl)Cl>[CH:32]([N:5]1[CH2:6][C@@H:1]2[CH2:7][C@H:4]1[CH2:3][N:2]2[C:8]1[N:13]=[C:12]([S:14][CH3:15])[N:11]=[C:10]([C:16]2[CH:21]=[CH:20][N:19]=[C:18]([NH:22][C@H:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH3:24])[CH:17]=2)[CH:9]=1)([CH3:34])[CH3:31]

Participants

6

Reactant 3

HCID 180AcetoneHCID 887MethanolHCID 68910742HCID 68910742, compound

Product 1

HCID 68910000HCID 68910000, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

The mixture of 0.13 g (0.31 mmol) {4-[6-(2,5-diaza-bicyclo[2.2.1]hept-2-yl)-2-methylsulfanyl-pyrimidin-4-yl]-pyridin-2-yl}-(1-phenyl-ethyl)-amine in 5 mL chloroform was treated with 0.2 mL (3.1 mmol) acetone, 0.19 g (3.1 mmol) NaBH3(CN) and 1 mL methanol. The mixture was stirred at rt for 15 h. MS showed all starting materials were converted. The mixture was diluted with 100 mL DCM, washed with 20 mL sat. NaHCO3, dried over anhydrous Na2SO4. After purification by chromatography, the title compound was obtained as a yellow solid. MS (ES+): 461 (M+H)+.

Workup

  1. washwashed with 20 mL sat. NaHCO3
  2. dry with materialdried over anhydrous Na2SO4
  3. customAfter purification by chromatography

Sources & evidence

ORD record
ord-433d3386d771433d9aef62fcf6a155a2
Source dataset
uspto-grants-2009_09
Patent number
US07582631B2

Reaction notes

Loading…