Dimethylformamide → HCID 86711139, compound

HRID 1472627Notes

Reaction equation

HRID 1472627 reaction equation
[Si:1]([O:8][CH:9]1[C:14]2=[N:15][C:16]([CH3:38])=[C:17]([CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][CH:25]([C:28]4[C:32]5[CH:33]=[CH:34][C:35]([OH:37])=[CH:36][C:31]=5[O:30][N:29]=4)[CH2:24][CH2:23]3)[C:18](=[O:19])[N:13]2[CH2:12][CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CN(C=O)C.C(=O)([O-])[O-].[K+].[K+].[C:50]([N:57](Br)[CH2:58][CH3:59])([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51]>CC(C)=O>[Si:1]([O:8][CH:9]1[C:14]2=[N:15][C:16]([CH3:38])=[C:17]([CH2:20][CH2:21][N:22]3[CH2:23][CH2:24][CH:25]([C:28]4[C:32]5[CH:33]=[CH:34][C:35]([O:37][CH2:59][CH2:58][NH:57][C:50](=[O:51])[O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[CH:36][C:31]=5[O:30][N:29]=4)[CH2:26][CH2:27]3)[C:18](=[O:19])[N:13]2[CH2:12][CH2:11][CH2:10]1)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 21185174HCID 21185174, compoundHCID 136377194HCID 136377194, compound

Product 1

HCID 86711139HCID 86711139, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 9-((tert-butyldimethylsilyl)oxy)-3-(2-(4-(6-hydroxybenzo[d]isoxazol-3-yl)piperidin-1-yl)ethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one, prepared as described in the previous step, (50 mg, 0.093 mmol) in acetone (0.5 mL) and DMF (0.5 mL) was treated with potassium carbonate (33.3 mg, 0.24 mmol) and N-Boc-2-bromoaminoethane (27 mg, 0.12 mmol), and the reaction mixture was stirred for 17 h at 60° C. under argon. The reaction mixture was evaporated at 40° C. under reduced pressure and dissolved in water (10 mL) and extracted with dichloromethane (3×10 mL). The organic layers were combined, dried over Na2SO4, filtered, and the solvent was evaporated yield the crude title compound. (ESI-MS (M+1) 682)

Workup

  1. customThe reaction mixture was evaporated at 40° C. under reduced pressure
  2. dissolutiondissolved in water (10 mL)
  3. extractionextracted with dichloromethane (3×10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-444013ff185d47149d1ebf14f596949a
Source dataset
uspto-grants-2015_04
Patent number
US09012648B2

Reaction notes

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