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

HRID 2100712Notes

Reaction equation

HRID 2100712 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][C:8]2[NH:9][C:10](=O)[C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:3]=1.O=P(Cl)(Cl)[Cl:21]>>[Cl:21][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]=[C:8]([NH:7][C:4]2[CH:3]=[C:2]([CH3:1])[NH:6][N:5]=2)[N:9]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 57799642HCID 57799642, compound

Product 1

HCID 57799635(1-chloro-isoquinolin-3-yl)-(5-methyl-1H-pyrazol-3-yl)-amineYield 61%

Conditions

Temperature
130 °C

Procedure

3-(5-Methyl-1H-pyrazol-3-ylamino)-2H-isoquinolin-1-one (7.4 g, 0.03 mol) and POCl3 (80 ml) were sealed in 4 bottles (20 ml). The mixture was heated at 130° C. for 15 minutes under microwave irradiation. The mixture was concentrated, and the residue was treated with 15 ml MeOH. The mixture was stirred for 2 hours at room temperature, and the solid was collected and dried to give desired product (4.7 g, 61% yield). LC-MS: 259 (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-5d3fd4356b5e4cbbbbe989772174fe66
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

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