N-(2-Oxoindolin-6-yl)acetamide → HCID 178474027, compound

HRID 1615232Notes

Reaction equation

HRID 1615232 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][C:6]([NH:11][C:12](=[O:14])[CH3:13])=[CH:7][CH:8]=2)[NH:3]1.[NH:15]1[C:19]2[CH:20]=[C:21]([CH:24]=O)[CH:22]=[CH:23][C:18]=2[N:17]=[N:16]1>>[NH:17]1[C:18]2[CH:23]=[CH:22][C:21](/[CH:24]=[C:10]3/[C:2](=[O:1])[NH:3][C:4]4[C:9]/3=[CH:8][CH:7]=[C:6]([NH:11][C:12](=[O:14])[CH3:13])[CH:5]=4)=[CH:20][C:19]=2[N:15]=[N:16]1

Participants

3

Reactant 2

HCID 2749839N-(2-Oxoindolin-6-yl)acetamideHCID 178519388HCID 178519388, compound

Product 1

HCID 178474027HCID 178474027, compound

Procedure

The title compound was synthesized according to the method described for Example A11B except substituting N-(2-oxoindolin-6-yl)acetamide (30 mg, 0.158 mmol) and 1H-benzo[d][1,2,3]triazole-6-carbaldehyde (26 mg, 0.174 mmol) to obtain 22 mg, 44%. 1H NMR (400 MHz, d6-DMSO) δ ˜16 (s, 1H), 10.60 (s, 1H), 10.10 (s, 1H), 8.23 (s, 1H), 8.01 (s, 1H), 7.73 (d, J=8.0 Hz, 1H), 7.64 (s, 1H), 7.51 (s, 1H), 7.47 (d, J=8.0 Hz, 1H), 6.86 (d, J=7.4 Hz, 1H), 2.02 (s, 3H); MS ESI 320.1 [M+H]+, calcd for [C17H13N5O2+H]+ 320.11.

Workup

  1. customto obtain 22 mg, 44%

Sources & evidence

ORD record
ord-4a3673af7fba483c90b8599ad119e0ee
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

Loading…