3-amino-6-{3-[(benzylamino)carbonyl]phenyl}-N-methoxy-N-methylpyrazine-2-carboxamide → 3-(5-Amino-6-formylpyrazin-2-yl)-N-benzylbenzamide

HRID 646770Notes

Reaction equation

[NH2:1][C:2]1[C:3]([C:24](N(OC)C)=[O:25])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([NH:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])[CH:9]=2)=[CH:6][N:7]=1>C1COCC1>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=2)[C:14]([NH:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15])=[N:4][C:3]=1[CH:24]=[O:25]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 3-amino-6-{3-[(benzylamino)carbonyl]phenyl}-N-methoxy-N-methylpyrazine-2-carboxamide (2.5 g, 6.4 mmol) in THF (20 mL) was cooled to 0° C. Under N2 lithium aluminum hydride (0.364g, 9.58 mmol) was added and the reaction was stirred at 0° C. for 1 h. The mixture was then quenched with H2O at 0° C. Removal of solids via filtration, concentration of the filtrate and dissolution of the solid residue in H2O followed by washing 3× with dichloromethane gave the product (1.90 g, 89% yield) with sufficient purity to be used without further purification.

Workup

additionUnder N2 lithium aluminum hydride (0.364g, 9.58 mmol) was added
customThe mixture was then quenched with H2O at 0° C
customRemoval of solids
filtrationvia filtration, concentration of the filtrate and dissolution of the solid residue in H2O
washby washing 3× with dichloromethane

Sources & evidence

ORD record: ord-fc70ea29a47043318182a00cd010cd45
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07704995B2

Reaction notes

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