N-methyl-2-pyrrolidone → HCID 53239545, compound

HRID 469588Notes

Reaction equation

HRID 469588 reaction equation
[N+:1](=[CH:3][C:4]([C:6]1([C:11]([F:14])([F:13])[F:12])[CH2:10][CH2:9][CH2:8][CH2:7]1)=O)=[N-:2].NN1[N:25]=[C:24]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]1=[O:33].CN1CCCC1=[O:40]>ClCCCl.CCOC(C)=O>[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([C:24]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17](=[O:33])[N:2]([NH:1][C:3](=[O:40])[CH2:4][C:6]3([C:11]([F:14])([F:13])[F:12])[CH2:10][CH2:9][CH2:8][CH2:7]3)[N:25]=2)=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 671613672-amino-4-(4-chlorophenyl)phthalazin-1(2H)-oneHCID 866537442-Diazo-1-(1-(trifluoromethyl)cyclopentyl)ethanone

Product 1

HCID 53239545HCID 53239545, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the above crude 2-diazo-1-(1-(trifluoromethyl)cyclopentyl)ethanone and the product from Example 86A in 1,2-dichloroethane and 1-methyl-2-pyrrolidinone was microwaved at 200° C. for 15 minutes, diluted with EtOAc, washed with saturated aqueous NaHCO3 and brine, dried (Na2SO4), and filtered. The residue was chromatographed on SiO2 (1-2% acetone/dichloromethane) to give the title compound as a white solid: 1H NMR (300 MHz, CDCl3) δ ppm 8.50-8.58 (m, 1H), 8.47-8.50 (bs, 1H), 7.78-7.86 (m, 2H), 7.67-7.75 (m, 1H), 7.52-7.57 (m, 2H), 7.48-7.52 (m, 2H), 2.67 (s, 2H), 2.07-2.18 (m, 2H), 1.94-2.04 (m, 2H), 1.67-1.84 (m, 4H); MS (ESI−) M/Z 448 (M−H)−.

Workup

  1. washwashed with saturated aqueous NaHCO3 and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customThe residue was chromatographed on SiO2 (1-2% acetone/dichloromethane)

Sources & evidence

ORD record
ord-22b2f042276c4829a6be200f933262fc
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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