Diisopropylethylamine → HCID 68456072, compound

HRID 2357673Notes

Reaction equation

HRID 2357673 reaction equation
[CH2:1]1[C@H:5]2[CH2:6][NH:7][CH2:8][CH2:9][N:4]2[C:3](=[O:10])[O:2]1.Cl[C:12]1[C:21]2[C:16](=[CH:17][C:18]([Cl:22])=[CH:19][CH:20]=2)[CH:15]=[N:14][N:13]=1.C(N(CC)C(C)C)(C)C>CN1CCCC1=O>[Cl:22][C:18]1[CH:17]=[C:16]2[C:21](=[CH:20][CH:19]=1)[C:12]([N:7]1[CH2:8][CH2:9][N:4]3[C:3](=[O:10])[O:2][CH2:1][C@H:5]3[CH2:6]1)=[N:13][N:14]=[CH:15]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 143223331,6-DichlorophthalazineHCID 27282253HCID 27282253, compound

Product 1

HCID 68456072HCID 68456072, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

The title compound was prepared by a method analogous to that described in Example 8 (Method A). A mixture of (R)-tetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one (0.800 g, 5.63 mmol), 1,6-dichlorophthalazine (0.516 g, 2.59 mmol) and N,N-diisopropylethylamine(1.40 mL, 8.04 mmol) in 3 mL 1-methyl-2-pyrolidone was heated at 140° C. After 4.5 h the reaction was cooled to RT, quenched with H2O and extracted with ethyl acetate (3×). The combined organic layers were dried over Na2SO4, filtered, evaporated onto silica gel and purified by flash chromatography eluting with 2 M NH3 in MeOH/CH2Cl2 (0:1→1:39) to give 1.18 g of a brown liquid. MS m/z: 305.1 [M+1].

Workup

  1. temperatureAfter 4.5 h the reaction was cooled to RT
  2. customquenched with H2O
  3. extractionextracted with ethyl acetate (3×)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated onto silica gel
  7. custompurified by flash chromatography
  8. washeluting with 2 M NH3 in MeOH/CH2Cl2 (0:1→1:39)

Sources & evidence

ORD record
ord-7f3603dbefa54c498afae6b577a91797
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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