Hydrogen Peroxide → HCID 68887205, compound

HRID 857901Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][C:24]=3[CH3:25])=[CH:15][C:16]([C:17]#[N:18])=[C:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1C(C(N)=O)=C2CN(S(C3SC(C4C=CC=CN=4)=CC=3)(=O)=[O:36])CCN2C=1C1C=CC=CC=1.[OH-].[Na+].OO>CO.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][C:24]=3[CH3:25])=[CH:15][C:16]([C:17](=[O:36])[NH2:18])=[C:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of a 2:3 mixture of 8-cyano-6-(4-methylpyridin-3-yl)-3,4-dihydro-1H-pyrrolo[1,2-a]pyrazine-2-carboxylic acid tert-butyl ester and 7-cyano-6-(4-methylpyridin-3-yl)-3,4-dihydro-1H-pyrrolo[1,2-a]pyrazine-2-carboxylic acid tert-butyl ester (18.30 g, Reference Example 31) in methanol (538 mL) at 10° C. was treated with a solution of sodium hydroxide (21.35 g) in water (4 mL) dropwise. The reaction mixture was then treated with a 27.5% w/w aqueous solution of hydrogen peroxide (9 mL). After stirring at 50° C. for 2 hours the reaction mixture was allowed to cool to room temperature. The insoluble material collected was washed with ethyl acetate to give the title compound (3.47 g) as a white solid, Rf 0.09 (ethyl acetate). 1H NMR [(CD3)2SO]: δ 8.51 (s, 1H), 7.77 (d, 1H), 7.40–7.25 (bs and d overlapping, 2H), 6.85–6.74 (bs and s overlapping, 2H), 4.83 (s, 2H), 3.98 (t, 2H), 3.66 (t, 2H), 2.50 (s, 3H) and 1.44 (s, 9H).

Workup

temperatureto cool to room temperature
customThe insoluble material collected
washwas washed with ethyl acetate

Sources & evidence

ORD record: ord-e5e43554324c4597b65c7506d797756b
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148215B2

Reaction notes

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