Phosphorus oxychloride → (1-chloro-6-methoxy-isoquinolin-3-yl)-(5-methyl-1H-pyrazol-3-yl)-amine

HRID 2100716Notes

Reaction equation

HRID 2100716 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=O)[NH:8][C:7]([NH:14][C:15]1[CH:19]=[C:18]([CH3:20])[NH:17][N:16]=1)=[CH:6]2.O=P(Cl)(Cl)[Cl:23]>>[Cl:23][C:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)[CH:6]=[C:7]([NH:14][C:15]2[CH:19]=[C:18]([CH3:20])[NH:17][N:16]=2)[N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 57799777HCID 57799777, compound

Product 1

HCID 57799674(1-chloro-6-methoxy-isoquinolin-3-yl)-(5-methyl-1H-pyrazol-3-yl)-amineYield 68%

Conditions

Temperature
150 °C

Procedure

6-Methoxy-3-(5-methyl-1H-pyrazol-3-ylamino)-2H-isoquinolin-1-one (4.7 g, 0.017 mol) and POCl3 (60 ml) were sealed in 3 different bottles (20 ml). The mixture was heated at 150° C. for 15 minutes under microwave irradiation. The mixture was concentrated, and the residue was treated with 15 ml MeOH, stirred for 2 hours at room temperature. The solid was collected and dried to give product (3.4 g, 68% yield). LC-MS: 289 (MH+)

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue was treated with 15 ml MeOH
  3. customThe solid was collected
  4. customdried

Sources & evidence

ORD record
ord-599bbcac7eaa4debbd093fce986ea869
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

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