5-Aminoindole → HCID 15521320, compound

HRID 1881668Notes

Reaction equation

HRID 1881668 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2Cl.[NH2:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][CH:18]=[CH:17]2>>[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[NH:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][CH:18]=[CH:17]2

Participants

3

Reactant 2

HCID 788675-AminoindoleHCID 111738094-Chloro-6-iodoquinazoline

Product 1

HCID 15521320HCID 15521320, compound

Procedure

JP-A-10-152477 describes a process for preparing a 4-arylaminoquinazoline compound from a quinazolin-4-one, which comprises the steps of chlorinating 4-iodoquinazolin-4-one using an excessive amount of oxalyl chloride to produce 6-iodo-4-chloroquinazoline (intermediate compound), concentrating the reaction product under reducing pressure to isolate the resulting product; reacting the 6-iodo-4-chloroquinazoline with 5-aminoindole to give 6-iodo-4 (5-indolylamino)quinazoline. Unfortunately, the yield is not high. Further, it should be noted that the intermediate compound, i.e., 4-chloroquinazoline compound, shows no satisfactory stability in the presence of water and no satisfactory resistance to heat. Accordingly, the compound should be handled carefully.

Workup

  1. concentrationconcentrating the reaction product
  2. customto isolate the resulting product

Sources & evidence

ORD record
ord-8af571ed92d9496799f655e9d5732b86
Source dataset
uspto-grants-2012_11
Patent number
US08318932B2

Reaction notes

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