Acetone → HCID 68910168, compound

HRID 729511Notes

Reaction equation

HRID 729511 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][CH2:24][C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=[CH:27][CH:26]=3)[CH:18]=2)[N:9]=1.[CH3:35][C:36]([CH3:38])=O.CO>C(Cl)(Cl)Cl.C(Cl)Cl>[CH:36]([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]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][CH2:24][C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=[CH:27][CH:26]=3)[CH:18]=2)[N:9]=1)([CH3:38])[CH3:35]

Participants

6

Reactant 3

HCID 180AcetoneHCID 887MethanolHCID 57832669HCID 57832669, compound

Product 1

HCID 68910168HCID 68910168, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

The mixture of 92 mg (0.2 mmol) {4-[5-(2,5-diaza-bicyclo[2.2.1]hept-2-yl)-imidazo[1,2-c]pyrimidin-7-yl]-pyridin-2-yl}-Naphthalen-1-ylmethyl-amine in 5 mL chloroform was treated with 0.12 g (2.0 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, and dried over anhydrous Na2SO4. After purification by chromatography, the title compound was obtained as a yellow solid.

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-5307bf96fcbb44568d7d1ce688d71947
Source dataset
uspto-grants-2009_09
Patent number
US07582631B2

Reaction notes

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