Diisopropylethylamine → HCID 136377194, compound

HRID 1472626Notes

Reaction equation

HRID 1472626 reaction equation
[Si:1]([O:8][CH:9]1[C:14]2=[N:15][C:16]([CH3:23])=[C:17]([CH2:20][CH2:21]Cl)[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].C(N(C(C)C)CC)(C)C.Cl.[NH:34]1[CH2:39][CH2:38][CH:37]([C:40]2[C:44]3[CH:45]=[CH:46][C:47]([OH:49])=[CH:48][C:43]=3[O:42][N:41]=2)[CH2:36][CH2:35]1>CO>[Si:1]([O:8][CH:9]1[C:14]2=[N:15][C:16]([CH3:23])=[C:17]([CH2:20][CH2:21][N:34]3[CH2:35][CH2:36][CH:37]([C:40]4[C:44]5[CH:45]=[CH:46][C:47]([OH:49])=[CH:48][C:43]=5[O:42][N:41]=4)[CH2:38][CH2:39]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]

Participants

5

Reactant 3

HCID 81531Diisopropylethylamine2×HCID 86711135HCID 86711135, compoundHCID 136377195HCID 136377195, compound

Product 1

HCID 136377194HCID 136377194, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 9-((tert-butyldimethylsilyl)oxy)-3-(2-chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one, prepared as described in the previous step, (0.5 g, 1.40 mmol) in methanol (25 mL) and diisopropylethylamine (732.83 μL, 4.20 mmol) was treated with 3-(piperidin-4-yl)benzo[d]isoxazol-6-ol hydrochloride salt (374.62 mg, 1.47 mmol), and the reaction mixture was stirred for 17 h at 60° C. under argon. Diisopropylethylamine (732.83 μL, 4.20 mmol) was added and the mixture was stirred additionally for 4 h at 60° C. The reaction mixture was evaporated under vacuum and the residue was taken up in water (25 mL), extracted with chloroform (3×25 mL). The combined organic layers were dried over MgSO4, filtered, and the solvent was removed under vacuum. The residue was purified by silica gel chromatography (elution with dichloromethane/methanol (98/2) to give the title compound (ESI-MS (M+1) 539).

Workup

  1. stirringthe mixture was stirred additionally for 4 h at 60° C
  2. customThe reaction mixture was evaporated under vacuum
  3. extractionextracted with chloroform (3×25 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was removed under vacuum
  7. customThe residue was purified by silica gel chromatography (
  8. washelution with dichloromethane/methanol (98/2)

Sources & evidence

ORD record
ord-cf484fbe3e5549598d1b3d6c24d833fd
Source dataset
uspto-grants-2015_04
Patent number
US09012648B2

Reaction notes

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