Ethanol → 6-[(4R)-4-{[(2S)-2-Hydroxy-4-(6-methoxy-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl)butyl]amino}-2-oxopyrrolidin-1-yl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one

HRID 1847066Notes

Reaction equation

C(O)C.[CH3:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[N:14]=[CH:13][C:12](=[O:15])[N:11]([CH2:16][CH2:17][C@H:18]3[CH2:20][O:19]3)[C:10]=2[N:21]=1.[NH2:22][C@H:23]1[CH2:27][N:26]([C:28]2[CH:29]=[CH:30][C:31]3[O:32][CH2:33][C:34](=[O:38])[NH:35][C:36]=3[N:37]=2)[C:25](=[O:39])[CH2:24]1.C(OC(=O)N[C@@H]1CC(=O)NC1)(C)(C)C>O>[OH:19][C@@H:18]([CH2:17][CH2:16][N:11]1[C:12](=[O:15])[CH:13]=[N:14][C:9]2[CH:8]=[CH:7][C:6]([O:5][CH3:4])=[N:21][C:10]1=2)[CH2:20][NH:22][C@H:23]1[CH2:27][N:26]([C:28]2[CH:29]=[CH:30][C:31]3[O:32][CH2:33][C:34](=[O:38])[NH:35][C:36]=3[N:37]=2)[C:25](=[O:39])[CH2:24]1

Participants

Conditions

Temperature: 80 °C

Procedure

In a mixed solvent (12 ml) of ethanol and water (9:1) were suspended 6-methoxy-4-{2-[(2S)-oxiran-2-yl]ethyl}pyrido[2,3-b]pyrazin-3(4H)-one (290 mg, 1.17 mmol) and 6-[(4R)-4-amino-2-oxopyrrolidin-1-yl]-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one (which was synthesized in the same manner as those of Reference Examples 20, 21 and 22, using the [(3R)-5-oxopyrrolidin-3-yl]carbamic acid tert-butyl ester synthesized with reference to WO2004/22536; 291 mg, 1.17 mmol). The obtained mixture was stirred in a sealed tube at 80° C. for 16 hours.

Workup

customwas synthesized in the same manner as those of Reference Examples 20, 21 and 22
customsynthesized with reference to WO2004/22536

Sources & evidence

ORD record: ord-4d9c9b9984ac4a7899437845f1f57787
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952010B2

Reaction notes

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