3-Aminopyridine → 9-methyl-6-oxo-N-(pyridin-3-yl)-6,7,8,9-tetrahydropyrido[3',2':4,5]pyrrolo[1,2-a]pyrazine-2-carboxamide

HRID 1521766Notes

Reaction equation

[CH3:1][C@H:2]1[N:7]2[C:8]3[N:14]=[C:13]([C:15]([OH:17])=O)[CH:12]=[CH:11][C:9]=3[CH:10]=[C:6]2[C:5](=[O:18])[NH:4][CH2:3]1.[CH:19]1[CH:20]=C[C:22]2[N:27](O)N=[N:25][C:23]=2[CH:24]=1.Cl.C(N=C=NCCCN(C)C)C.NC1C=NC=CC=1>CN(C=O)C.CN(C1C=CN=CC=1)C.CO.CCOCC>[CH3:1][CH:2]1[N:7]2[C:8]3[N:14]=[C:13]([C:15]([NH:25][C:23]4[CH:22]=[N:27][CH:20]=[CH:19][CH:24]=4)=[O:17])[CH:12]=[CH:11][C:9]=3[CH:10]=[C:6]2[C:5](=[O:18])[NH:4][CH2:3]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of 9-methyl-6-oxo-6,7,8,9-tetrahydropyrido[3′,2′:4,5]pyrrolo[1,2-a]pyrazine-2-carboxylic acid (Intermediate J, 47 mg, 0.19 mmol) and HOBt (31 mg, 0.23 mmol) in DMF (0.5 mL) is added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (44 mg, 0.23 mmol), followed by 3-aminopyridine (22 mg, 0.23 mmol) and DMAP (2.8 mg, 0.023 mmol). The mixture is stirred at 60° C. under a continuous stream of nitrogen, which slowly concentrates the solution. After being stirred for 5 h, the mixture was warmed to 80° C. and stirred overnight. The reaction mixture is diluted with methanol (0.5 mL) and ether (1 mL). The resultant precipitate is collected by filtration to afford the title compound as a dark yellow solid (21 mg, 34%).

Workup

stirringAfter being stirred for 5 h
temperaturethe mixture was warmed to 80° C.
stirringstirred overnight
filtrationThe resultant precipitate is collected by filtration

Sources & evidence

ORD record: ord-5f127b47b3c94b1789d68b517f589589
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073926B2

Reaction notes

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