1H-Indazol-6-amine → HCID 10270538, compound

HRID 1591609Notes

Reaction equation

HRID 1591609 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=2[CH3:16])[N:3]=1.[NH2:17][C:18]1[CH:26]=[C:25]2[C:21]([CH:22]=[N:23][NH:24]2)=[CH:20][CH:19]=1.C(N(C(C)C)CC)(C)C>O1CCCC1>[Cl:8][C:6]1[N:5]=[C:4]([C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=2[CH3:16])[N:3]=[C:2]([NH:17][C:18]2[CH:26]=[C:25]3[C:21]([CH:22]=[N:23][NH:24]3)=[CH:20][CH:19]=2)[N:7]=1

Participants

5

Reactant 3

HCID 814231H-Indazol-6-amineHCID 81531DiisopropylethylamineHCID 858270322,4-Dichloro-6-(5-chloro-2-methyl-phenyl)-[1,3,5]triazine

Product 1

HCID 10270538HCID 10270538, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2,4-dichloro-6-(5-chloro-2-methyl-phenyl)-[1,3,5]triazine (1 g, 3.6 mmol), 6-aminoindazole (0.5 g, 3.7 mmol), tetrahydrofuran (10 ml), and diisopropylethylamine (0.65 ml, 3.7 mmol) was stirred for 1 hour. After concentrating under reduced pressure, the residue was treated with water (25 ml) and stirred for 10 minutes. The solid was filtered, treated with hydrochloric acid (1 M, 10 ml), stirred vigorously for 10 minutes, and filtered. The solid was purified by flash chromatography on silica eluting with 5% methanol-dichloromethane to yield the title compound (600 mg, 45% yield). 1H NMR (DMSO-d6) 13.04 (br s, 1H), 10.90-10.97 (m, 1H), 8.12 (s, 1H), 8.02 (s, 1H), 7.71 (m, 2H), 7.53 (m, 1H), 7.41 (m, 1H), 7.34 (m, 1H), 2.50-2.54 (m, 3H).

Workup

  1. concentrationAfter concentrating under reduced pressure
  2. additionthe residue was treated with water (25 ml)
  3. stirringstirred for 10 minutes
  4. filtrationThe solid was filtered
  5. additiontreated with hydrochloric acid (1 M, 10 ml)
  6. stirringstirred vigorously for 10 minutes
  7. filtrationfiltered
  8. customThe solid was purified by flash chromatography on silica eluting with 5% methanol-dichloromethane

Sources & evidence

ORD record
ord-df387bd2e21a465491c58462bce5c501
Source dataset
uspto-grants-2007_11
Patent number
US07291616B2

Reaction notes

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