N-methyl-2-pyrrolidone → HCID 70975809, compound

HRID 535623Notes

Reaction equation

HRID 535623 reaction equation
[NH2:1][N:2]1[N:11]=[C:10]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:18].[CH2:19]1[CH:24]2[CH2:25][C:26]3([C:28]([O-])=[CH:29][N+]#N)[CH2:27][CH:20]1[CH2:21][CH:22]3[CH2:23]2.CN1CCCC1=[O:39]>ClCCCl.CCOC(C)=O>[CH2:23]1[CH:22]2[C:26]3([CH2:28][C:29]([NH:1][N:2]4[N:11]=[C:10]([N:12]5[CH2:17][CH2:16][O:15][CH2:14][CH2:13]5)[C:9]5[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=5)[C:3]4=[O:18])=[O:39])[CH2:27][CH:20]([CH2:19][CH:24]1[CH2:25]3)[CH2:21]2

Participants

6

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 709761042-amino-4-morpholinophthalazin-1(2H)-oneHCID 178514372HCID 178514372, compound

Product 1

HCID 70975809HCID 70975809, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the product from Example 1B (48.5 mg, 0.197 mmol) and the product from Example 210A (0.0384 g, 0.202 mmol) in 1,2-dichloroethane (0.6 mL) and 1-methyl-2-pyrrolidinone (0.20 mL) was microwaved at 180° C. for 20 minutes, diluted with EtOAc, washed with sat NaHCO3 and brine, dried (Na2SO4), filtered, and chromatographed (12% EtOAc/DCM) to give 31.2 mg of the title compound as a tan solid: 1H NMR (300 MHz, DMSO-d6) δ 11.11 (s, 1H), 8.34-8.27 (m, 1H), 8.06-7.93 (m, 2H), 7.93-7.84 (m, 1H), 3.85-3.78 (m, 4H), 3.12-3.04 (m, 4H), 2.44 (s, 2H), 2.33 (t, J=6.6, 1H), 2.17 (s, 2H), 1.83-1.46 (m, 10H); MS (ESI+) M/Z 409 (M+H)+.

Workup

  1. washwashed
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customchromatographed (12% EtOAc/DCM)

Sources & evidence

ORD record
ord-699463927ba54f76895db3b2b29730ca
Source dataset
uspto-grants-2014_10
Patent number
US08859549B2

Reaction notes

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