Hydrochloric Acid → 4-Amino-N-{3-[7-(2,2-dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-phenyl}-benzenesulfonamide

HRID 1677511Notes

Reaction equation

[CH3:1][C:2]([CH3:35])([CH3:34])[C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([C:14]3[CH:15]=[C:16]([NH:20][S:21]([C:24]4[CH:29]=[CH:28][C:27]([NH:30]C(=O)C)=[CH:26][CH:25]=4)(=[O:23])=[O:22])[CH:17]=[CH:18][CH:19]=3)[N:12]=2)[NH:7][CH:6]=1)=[O:4].Cl>[OH-].[Na+].O>[NH2:30][C:27]1[CH:28]=[CH:29][C:24]([S:21]([NH:20][C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([C:11]3[N:12]=[C:13]4[C:5]([C:3](=[O:4])[C:2]([CH3:34])([CH3:1])[CH3:35])=[CH:6][NH:7][C:8]4=[N:9][CH:10]=3)[CH:15]=2)(=[O:23])=[O:22])=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 100 °C

Procedure

In a flask N-(4-{3-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-phenylsulfamoyl}-phenyl)-acetamide 0.034 gm (0.069 mM), 1 ml water and 10 drops 3M aqueous sodium hydroxide was added and the mixture heated to 100° C. for two hours. Water (20 ml) was added and the pH adjusted to 8 with hydrochloric acid and much solid formed. The mixture was extracted three times with ethyl acetate, the ethyl acetate dried over magnesium sulfate to give 4-Amino-N-{3-[7-(2,2-dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-phenyl}-benzenesulfonamide 0.023 gm (0.051 mM, 74% yield) M+1 450 m.p. 285-286° C.

Workup

customformed
extractionThe mixture was extracted three times with ethyl acetate
dry with materialthe ethyl acetate dried over magnesium sulfate

Sources & evidence

ORD record: ord-c02373cb2ce2430b818897b99d562701
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008298B2

Reaction notes

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