Phosphorus oxychloride → HCID 57799568, compound

HRID 2100732Notes

Reaction equation

HRID 2100732 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][O:16][CH3:17])[C:9](O)=[N:8][C:7]([NH:19][C:20]1[CH:24]=[C:23]([CH3:25])[NH:22][N:21]=1)=[CH:6]2.O=P(Cl)(Cl)[Cl:28]>>[Cl:28][C:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:12]([O:13][CH2:14][CH2:15][O:16][CH3:17])[CH:11]=2)[CH:6]=[C:7]([NH:19][C:20]2[CH:24]=[C:23]([CH3:25])[NH:22][N:21]=2)[N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178496072HCID 178496072, compound

Product 1

HCID 57799568HCID 57799568, compoundYield 62.7%

Conditions

Temperature
160 °C

Procedure

A mixture of 6-Methoxy-7-(2-methoxy-ethoxy)-3-(5-methyl-1H-pyrazol-3-ylamino)-isoquinolin-1-ol (1.0 g, 1.45 mmol) in POCl3 (20 ml) was sealed in 2 microwave process vial (20 ml). The mixture was heated at 160° C. for 30 minutes under microwave irradiation. After removal of excess solvent, the residue was poured into ice-water, 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 solid (0.33 g, 62.7%). LC-MS: m/e 363 (MH+).

Workup

  1. customwas sealed in 2 microwave process vial (20 ml)
  2. customAfter removal of excess solvent
  3. additionthe residue was poured into ice-water
  4. extractionextracted by EtOAc
  5. concentrationThe organic layer was concentrated
  6. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-d8c1e57ac10f4aafb60ca15ead3528d8
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

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