Acetone → HCID 68905789, compound

HRID 729510Notes

Reaction equation

HRID 729510 reaction equation
[CH:1]12[CH2:7][CH:4]([NH:5][CH2:6]1)[CH2:3][N:2]2[C:8]1[N:13]2[CH:14]=[CH:15][N:16]=[C:12]2[CH:11]=[C:10]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][CH:24]([CH3:28])[CH:25]([CH3:27])[CH3:26])[CH:18]=2)[N:9]=1.[CH3:29][C:30]([CH3:32])=O.CO>C(Cl)(Cl)Cl.C(Cl)Cl>[CH3:28][CH:24]([NH:23][C:19]1[CH:18]=[C:17]([C:10]2[N:9]=[C:8]([N:2]3[CH2:3][C@@H:4]4[CH2:7][C@H:1]3[CH2:6][N:5]4[CH:30]([CH3:32])[CH3:29])[N:13]3[CH:14]=[CH:15][N:16]=[C:12]3[CH:11]=2)[CH:22]=[CH:21][N:20]=1)[CH:25]([CH3:27])[CH3:26]

Participants

6

Reactant 3

HCID 180AcetoneHCID 887MethanolHCID 57832687HCID 57832687, compound

Product 1

HCID 68905789HCID 68905789, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

The mixture of 25 mg (0.066 mmol) {4-[5-(2,5-diaza-bicyclo[2.2.1]hept-2-yl-)-imidazo[1,2-c]pyrimidin-7-yl]-pyridin-2-yl}-(1,2-dimethyl-propyl)-amine in 5 mL chloroform was treated with 38 mg (0.66 mmol) acetone, 41 mg (0.66 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, obtained the title compound as a yellow solid. MS (ES+): 420 (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-8b1b00b8492048c1a753fb981149a95b
Source dataset
uspto-grants-2009_09
Patent number
US07582631B2

Reaction notes

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