Phosphorus oxychloride → HCID 57799586, compound

HRID 2100742Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][O:19][CH3:20])[C:12](O)=[N:11][C:10]([NH:22][C:23]1[CH:27]=[C:26]([CH3:28])[NH:25][N:24]=1)=[CH:9]2.O=P(Cl)(Cl)[Cl:31]>>[Cl:31][C:12]1[C:13]2[C:8](=[CH:7][C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[C:15]([O:16][CH2:17][CH2:18][O:19][CH3:20])[CH:14]=2)[CH:9]=[C:10]([NH:22][C:23]2[CH:27]=[C:26]([CH3:28])[NH:25][N:24]=2)[N:11]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 178496070HCID 178496070, compound

Product 1

HCID 57799586HCID 57799586, compoundYield 37.6%

Conditions

Temperature: 170 °C

Procedure

A mixture of 6,7-Bis-(2-methoxy-ethoxy)-3-(5-methyl-1H-pyrazol-3-ylamino)-isoquinolin-1-ol (1.8 g, 4.64 mmol) in POCl3 (15 ml) was sealed in microwave process vial (20 ml). The mixture was heated at 170° C. for 30 minutes under microwave irradiation. After removal of solvent, the ice water was added to the residue, and the mixture was neutralized by 2M NaOH, extracted by EtOAc. The organic layer was concentrated and the residue was purified by flash column chromatography to give product as a solid (0.7 g, 37.6%). LC-MS: m/e 408 (MH+).

Workup

customwas sealed in microwave process vial (20 ml)
customAfter removal of solvent
additionthe ice water was added to the residue
extractionextracted by EtOAc
concentrationThe organic layer was concentrated
customthe residue was purified by flash column chromatography

Sources & evidence

ORD record: ord-6fb0ae87f71549d49fe99859de727493
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572809B2

Reaction notes

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