3-Chloroaniline → HCID 178418828, compound

HRID 480594

Reaction equation

HRID 480594 reaction equation
Cl[C:2]1[N:11]=[C:10]([NH:12][C:13]2[NH:14][N:15]=[C:16]([CH3:18])[CH:17]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[Cl:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][CH:26]=1)[NH2:23].C([O-])([O-])=O.[K+].[K+]>C(O)(C)(C)C>[Cl:19][C:20]1[CH:21]=[C:22]([NH:23][C:2]2[N:11]=[C:10]([NH:12][C:13]3[NH:14][N:15]=[C:16]([CH3:18])[CH:17]=3)[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)[CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 79323-ChloroanilineHCID 11430Potassium CarbonateHCID 219391632-Chloro-n-(5-methyl-1h-pyrazol-3-yl)quinazolin-4-amine

Product 1

HCID 178418828HCID 178418828, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

The above-prepared (2-chloroquinazolin-4-yl)-(5-methyl-2H-pyrazol-3-yl)-amine (155 mg, 0.6 mmol) and 3-chloroaniline (0.316 mL, 2.99 mmol) are refluxed in tert-butanol (3 mL) over 20 h. The mixture is concentrated in vacuo and the residue is suspended in EtOH/H2O (1 mL/3 mL). K2CO3 (83 mg, 0.6 mmol) is added and the suspension is stirred for 2 h at room temperature. The solid that forms is collected and dried under vacuum to give the product [2-(3-chlorophenylamino)-quinazolin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. customThe solid that forms is collected
  3. customdried under vacuum

Sources & evidence

ORD record
ord-edd467e3566943ee8f69887a304e3e5a
Source dataset
uspto-grants-2003_11
Patent number
US06653300B2

Linked notes

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