Succinic anhydride → 4-oxo-4-(1-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazin-2(1H)-yl)butanoic acid

HRID 909253

Reaction equation

HRID 909253 reaction equation
[C:1]1([CH:7]2[NH:12][CH2:11][CH2:10][N:9]3[CH:13]=[CH:14][CH:15]=[C:8]23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(CC)CC.[C:23]1(=[O:29])[O:28][C:26](=[O:27])[CH2:25][CH2:24]1.CC(=O)OCC.CO>CC#N.CC(=O)OCC>[O:29]=[C:23]([N:12]1[CH2:11][CH2:10][N:9]2[CH:13]=[CH:14][CH:15]=[C:8]2[CH:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:24][CH2:25][C:26]([OH:28])=[O:27]

Participants

7

Reactant 4

HCID 7922Succinic anhydrideHCID 8471TriethylamineHCID 27709101-phenyl-1H,2H,3H,4H-pyrrolo(1,2-a)pyrazineHCID 21584119Ethylacetate methanol

Product 1

HCID 427793334-oxo-4-(1-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazin-2(1H)-yl)butanoic acidYield 44%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Phenyl-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine (A2) (396 mg, 2.0 mmol) and NEt3 (277 μl, 2.0 mmol) were added to a suspension of succinic anhydride (176 mg, 1.76 mmol) in MeCN (28 ml), and stirring was carried out for 16 h at RT. The mixture was then diluted with EA (30 ml) and washed with 2N hydrochloric acid (2×5 ml). The organic phase was dried over MgSO4, filtered and concentrated in vacuo. The resulting residue was taken up in EA (50 ml) and again washed with 2N hydrochloric acid (20 ml) and then with a sat. aq. sodium carbonate solution (2×30 ml). The organic phase was again dried over MgSO4, filtered and concentrated in vacuo. CC (EA/MeOH 3:1) with the residue yielded 230 mg (0.77 mmol, 44%) of 4-oxo-4-(1-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazin-2(1H)-yl)butanoic acid (S3).

Workup

  1. washwashed with 2N hydrochloric acid (2×5 ml)
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. washagain washed with 2N hydrochloric acid (20 ml)
  6. dry with materialThe organic phase was again dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-471bfbf9f1d94d26aafab6e253d4ad81
Source dataset
uspto-grants-2011_09
Patent number
US08017772B2

Linked notes

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