tert-Butyl (2-oxoindolin-5-yl)carbamate → HCID 178452630, compound

HRID 1615338Notes

Reaction equation

HRID 1615338 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:8]=2)[NH:3]1.[N:19]1[CH:24]=[CH:23][C:22](/[CH:25]=[CH:26]/[C:27]2[C:35]3[C:30](=[CH:31][C:32]([CH:36]=O)=[CH:33][CH:34]=3)[NH:29][N:28]=2)=[CH:21][CH:20]=1>>[O:1]=[C:2]1[NH:3][C:4]2[C:9](/[C:10]/1=[CH:36]\[C:32]1[CH:31]=[C:30]3[C:35]([C:27](/[CH:26]=[CH:25]/[C:22]4[CH:21]=[CH:20][N:19]=[CH:24][CH:23]=4)=[N:28][NH:29]3)=[CH:34][CH:33]=1)=[CH:8][C:7]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[CH:6][CH:5]=2

Participants

3

Reactant 2

HCID 53971753tert-Butyl (2-oxoindolin-5-yl)carbamateHCID 86651943HCID 86651943, compound

Product 1

HCID 178452630HCID 178452630, compoundYield 76%

Procedure

The title compound (102 mg, 76%) was synthesized as orange-yellow solid according to the method described for Example A11B from tert-butyl 2-oxoindolin-5-ylcarbamate (70 mg, 0.282 mmol) and (E)-3-(2-(pyridin-4-yl)vinyl)-1H-indazole-6-carbaldehyde (70 mg, 0.282 mmol). 1H NMR (400 MHz, d6-DMSO) δ 13.53 (s, 1H), 10.47 (s, 1H), 9.14 (s, 1H), 8.55 (d, J=6.5 Hz, 2H), 8.33 (d, J=8.8 Hz, 1H), 7.88-7.83 (m, 3H), 7.74 (s, 2H), 7.69 (d, J=6.5 Hz, 2H), 7.56-7.50 (m, 2H), 6.75 (d, J=8.2 Hz, 1H), 1.34 (s, 9H); MS ESI 480.3 [M+H]+, calcd for [C28H25N5O3+H]+ 480.20.

Sources & evidence

ORD record
ord-c92a4291ffc248ef9731dc60bacd98f1
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

Loading…