6-Chloro-1,3-dihydroindol-2-one → HCID 178517232, compound

HRID 1615220Notes

Reaction equation

HRID 1615220 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[NH:12]1[C:16]2[CH:17]=[CH:18][C:19]([CH:21]=O)=[CH:20][C:15]=2[N:14]=[N:13]1>>[NH:12]1[C:16]2[CH:17]=[CH:18][C:19](/[CH:21]=[C:6]3/[C:7](=[O:11])[NH:8][C:9]4[C:5]/3=[CH:4][CH:3]=[C:2]([Cl:1])[CH:10]=4)=[CH:20][C:15]=2[N:14]=[N:13]1

Participants

3

Reactant 2

HCID 7363446-Chloro-1,3-dihydroindol-2-oneHCID 178519382HCID 178519382, compound

Product 1

HCID 178517232HCID 178517232, compound

Procedure

The title compound was synthesized according to the method described for Example A1 except reacting 6-chlorooxindole (36 mg, 0.216 mmol) with 1H-benzo[d][1,2,3]triazole-5-carbaldehyde (35 mg, 0.238 mmol) to obtain 32 mg, 51%. 1H NMR (400 MHz, d6-DMSO) δ 15.95 (s, 1H), 10.81 (s, 1H), 8.27 (bs, 1H), 8.04 (bs, 1H), 7.85 (s, 1H), 7.76 (bs, 1H), 7.49 (d, J=8.8 Hz, 1H), 6.91 (bs, 2H); MS ESI 297.0 [M+H]+, calcd for [C15H9ClN4O+H]+ 297.05.

Workup

  1. customto obtain 32 mg, 51%

Sources & evidence

ORD record
ord-520eebb6a7d1443b8712b2e173433913
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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