Ammonia → tert-butyl 8-carbamoyl-6-chloro-7-(3-cyanophenyl)-3,4-dihydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate

HRID 1629999Notes

Reaction equation

[Cl:1][C:2]1[N:6]2[CH2:7][CH2:8][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10][C:5]2=[C:4]([C:18]([N:20]2C=CN=C2)=[O:19])[C:3]=1[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]#[N:32])[CH:26]=1.N.O>CN(C)C=O>[C:18]([C:4]1[C:3]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]#[N:32])[CH:26]=2)=[C:2]([Cl:1])[N:6]2[CH2:7][CH2:8][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10][C:5]=12)(=[O:19])[NH2:20]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 3.28 g (7.26 mmol) of tert-butyl 6-chloro-7-(3-cyanophenyl)-8-(1H-imidazol-1-ylcarbonyl)-3,4-dihydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate in 4 ml of dimethylformamide in an autoclave are added 6 ml of 33% aqueous ammonia. The mixture is stirred for 3 hours at 110° C. and, after cooling, is then poured into 80 ml of water and the solid is separated out by filtration. The solid is taken up in dichloromethane, the solution is then dried over sodium sulfate and the solvent is evaporated off under reduced pressure to give 2.9 g of tert-butyl 8-carbamoyl-6-chloro-7-(3-cyanophenyl)-3,4-dihydropyrrolo[1,2-a]pyrazine-2(1H)-carboxylate after drying.

Workup

temperatureafter cooling
customthe solid is separated out by filtration
dry with materialthe solution is then dried over sodium sulfate
customthe solvent is evaporated off under reduced pressure

Sources & evidence

ORD record: ord-b03aa91bab8945c9a41f40181a3bf172
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791119B2

Reaction notes

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