Triethylamine → HCID 22724284, compound

HRID 2231044Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([N:8]2[C:13](=[O:14])[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:11][C:10]3[CH:22]=[CH:23][CH:24]=[N:25][C:9]2=3)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[O:33]1[CH2:38][CH2:37][N:36]([C:39](Cl)=[O:40])[CH2:35][CH2:34]1.C(=O)(O)[O-].[Na+]>CN(C)C1C=CN=CC=1.O1CCOCC1.C(OCC)(=O)C>[CH2:15]([C:12]1[C:13](=[O:14])[N:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:39]([N:36]3[CH2:37][CH2:38][O:33][CH2:34][CH2:35]3)=[O:40])[CH:3]=2)[C:9]2[N:25]=[CH:24][CH:23]=[CH:22][C:10]=2[N:11]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-(3-aminophenyl)-2-benzyl-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (339 mg), triethylamine (0.18 ml), 4-dimethylaminopyridine (5 mg) and morpholinocarbonyl chloride (0.15 ml) in 1,4-dioxane (4 ml) was stirred at 80° C. for 2 hours. Then the mixture was poured into a mixture of ethyl acetate and aqueous sodium bicarbonate. The organic phase was separated, washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel column (ethyl acetate) to give 2-benzyl-4-[3-(morpholinocarbonylamino)phenyl]-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (242 mg).

Workup

customThe organic phase was separated
washwashed with aqueous sodium bicarbonate and brine
dry with materialdried over magnesium sulfate
concentrationconcentrated
customThe residue was chromatographed on silica gel column (ethyl acetate)

Sources & evidence

ORD record: ord-2e40ab02404244e48054010de5f3afb0
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06426345B1

Reaction notes

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