Tetrahydrofuran → HCID 57799756, compound

HRID 2101104Notes

Reaction equation

[CH:1]([O:4][C:5]1[C:14]2[C:9](=[CH:10][C:11](OS(C(F)(F)F)(=O)=O)=[CH:12][CH:13]=2)[CH:8]=[C:7]([NH:23][C:24]2[CH:28]=[C:27]([CH3:29])[NH:26][N:25]=2)[N:6]=1)([CH3:3])[CH3:2].[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1.C1CCN2C(=NCCC2)CC1.C1C[O:50][CH2:49]C1>CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:1]([O:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([C:49]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)=[O:50])=[CH:12][CH:13]=2)[CH:8]=[C:7]([NH:23][C:24]2[CH:28]=[C:27]([CH3:29])[NH:26][N:25]=2)[N:6]=1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 150 °C

Procedure

A 2.0˜5.0 mL process vial was charged with trifluoro-methanesulfonic acid 1-isopropoxy-3-(5-methyl-1H-pyrazol-3-ylamino)-isoquinolin-6-yl ester (56.2 mg, 1 mmol), Pd(OAc)2 (4 mg), Mo(CO)6 (26.4 mg), morpholine (26.0 mg), DBU (45 mg), and dry THF (2 mL). The vial was immediately capped under air and heated at 150° C. for 15 min under microwave irradiation. After cooling, the reaction mixture was filtered through a short silica gel column, and the solvent was removed under reduced pressure. The residue was sent to prep-HPLC to give 5 mg of [1-Isopropoxy-3-(5-methyl-1H-pyrazol-3-ylamino)-isoquinolin-6-yl]-morpholin-4-yl-methanone as a yellow solid. LC-MS m/e 396 (MH+).

Workup

customThe vial was immediately capped under air
temperatureAfter cooling
filtrationthe reaction mixture was filtered through a short silica gel column
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-aa184beb87334dde80df4742cd90a639
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572809B2

Reaction notes

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