2-chloro-3-(morpholin-4-yl)quinoxaline → HCID 21994839, compound

HRID 1197441Notes

Reaction equation

CC(C)([O-])C.[K+].Cl[C:8]1[C:17]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[N:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1.[CH:24]1([C:27]2[O:31][N:30]=[C:29]([CH2:32][N+:33]#[C-:34])[N:28]=2)[CH2:26][CH2:25]1>CN(C=O)C>[CH:24]1([C:27]2[O:31][N:30]=[C:29]([C:32]3[N:33]=[CH:34][N:9]4[C:10]5[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=5)[N:16]=[C:17]([N:18]5[CH2:23][CH2:22][O:21][CH2:20][CH2:19]5)[C:8]=34)[N:28]=2)[CH2:26][CH2:25]1

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of potassium t-butoxide (3.7 g, 32 mmol) in dry DMF (25 ml) was added to a stirred solution of 2-chloro-3-morpholino-quinoxaline (4 g, 16 mmol) and 5-cyclopropyl-3-isocyanomethyl-1,2,4-oxadiazole in dry DMF (50 ml), the temperature being kept at 0°-5° C. Then the temperature was raised to 20° C. and the solvent was evaporated in vacuo. The residue was partitioned between water (50 ml) and dichloromethane (50 ml). The organic phase was dried and evaporated and the residue was triturated with a small amount of ethyl acetate. The resulting crystalline product was collected by filtration and dried to give 3.2 g of the title compound, m.p. 169°-173° C. (Compound 9).

Workup

custombeing kept at 0°-5° C
customthe solvent was evaporated in vacuo
customThe residue was partitioned between water (50 ml) and dichloromethane (50 ml)
customThe organic phase was dried
customevaporated
customthe residue was triturated with a small amount of ethyl acetate
filtrationThe resulting crystalline product was collected by filtration
customdried

Sources & evidence

ORD record: ord-636d70258a344a2e81688b4a264a6fcf
Source dataset: uspto-grants-1994_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05276028

Reaction notes

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