Cesium carbonate → 4-(4-(5-(hexahydropyrrolo[3,4-b]pyrrol-5(1H)-yl)pyrido[4,3-b]pyrazin-7-yl)phenyl)morpholine

HRID 57608

Reaction equation

Cl[C:2]1[N:11]=[C:10]([N:12]2[CH2:19][CH:18]3[CH:14]([NH:15][CH2:16][CH2:17]3)[CH2:13]2)[C:9]2[C:4](=[N:5][CH:6]=[CH:7][N:8]=2)[CH:3]=1.[O:20]1[CH2:25][CH2:24][N:23]([C:26]2[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=2)[CH2:22][CH2:21]1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH:15]1[CH2:16][CH2:17][CH:18]2[CH2:19][N:12]([C:10]3[C:9]4[C:4](=[N:5][CH:6]=[CH:7][N:8]=4)[CH:3]=[C:2]([C:29]4[CH:28]=[CH:27][C:26]([N:23]5[CH2:22][CH2:21][O:20][CH2:25][CH2:24]5)=[CH:31][CH:30]=4)[N:11]=3)[CH2:13][CH:14]12

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 7-chloro-5-(hexahydropyrrolo[3,4-b]pyrrol-5(1H)-yl)pyrido[4,3-b]pyrazine (47 mg, 0.17 mmol), 4-morpholinophenylboronic acid (105 mg, 0.51 mmol), and PdCl2(dppf) (10 mg), Cs2CO3 (130 mg, 0.51 mmol) in dioxane (5 mL) was sealed in a microwave reaction cube, stirred at 180° C. for 60 minutes in a microwave reactor, cooled to ambient temperature, concentrated under reduced pressure, and the residue was purified by chromatography to give the title compound. MS (m/z): 403 (M+H)+.

Workup

customwas sealed in a microwave reaction cube
temperaturecooled to ambient temperature
concentrationconcentrated under reduced pressure
customthe residue was purified by chromatography

Sources & evidence

ORD record: ord-8d63c4ea98244ab6add05a9264af3efe
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434726B2

Linked notes

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