5-Aminoindole → HCID 70241132, compound

HRID 1975976Notes

Reaction equation

HRID 1975976 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=[CH:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]=[CH:14][NH:13][C:12]3=O)=[CH:3][CH:2]=1.[NH2:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[NH:26][CH:25]=[CH:24]2>>[NH:26]1[C:27]2[C:23](=[CH:22][C:21]([NH:20][C:12]3[C:11]4[C:16](=[CH:17][CH:18]=[C:9]([CH:8]=[CH:7][C:4]5[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=5)[CH:10]=4)[N:15]=[CH:14][N:13]=3)=[CH:29][CH:28]=2)[CH:24]=[CH:25]1

Participants

3

Reactant 2

HCID 788675-AminoindoleHCID 1360386686-[2-(4-Pyridinyl)ethenyl]-4(3H)-quinazolinone

Product 1

HCID 70241132HCID 70241132, compoundYield 74.3%

Conditions

Temperature
60 °C

Procedure

The title compound (250 mg, 1.0 mmol) from Example 20 was activated in an analogous method to Example 21 and combined with 5 -aminoindole (171 mg, 1.3 mmol). The reaction mixture was heated at 60° C. overnight and then cooled to room temperature. The resin was filtered off and the solution was concentrated in vacuo. The crude residue was chromatographed on silica gel in 10% acetone/ethyl acetate to provide 270 mg (74%) of the product.

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe resin was filtered off
  3. concentrationthe solution was concentrated in vacuo
  4. customThe crude residue was chromatographed on silica gel in 10% acetone/ethyl acetate

Sources & evidence

ORD record
ord-2b3dc3c24c4a44a59607eea7b495a385
Source dataset
uspto-grants-2001_05
Patent number
US06225318B1

Reaction notes

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