Octahydropyrrolo[1,2-a]piperazin-6-one → 2-(6-chlorophthalazin-1-yl)-tetrahydropyrrolo[1,2-a]pyrazin-6(1H,2H,7H)-one

HRID 2357679Notes

Reaction equation

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

Participants

Conditions

Temperature: 135 °C

Procedure

A mixture of tetrahydropyrrolo[1,2-a]pyrazin-6(1H,2H,7H)-one (Med. Chem. Res., 7:301 (1997); 0.983 g, 7.01 mmol), 1,6-dichlorophthalazine (1.36 g, 6.83 mmol) and TEA (2.00 mL, 14.3 mmol) in 18 mL of CH3CN was heated at 135° C. for 30 min in a microwave oven. The reaction mixture was concentrated onto silica gel and purified using flash chromatography eluting with 2M NH3 in MeOH:CH2Cl2 (0:1→3:97) to give 404 mg (20%) an orange foam/amorphous solid. MS m/z: 303.1 [M+1].

Workup

concentrationThe reaction mixture was concentrated onto silica gel
custompurified
washeluting with 2M NH3 in MeOH:CH2Cl2 (0:1→3:97)

Sources & evidence

ORD record: ord-2b49017f92764a2599e06cb63865aea4
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759337B2

Reaction notes

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