4-Cyanobenzaldehyde → (Z)-4-(((2-(5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)ethyl)amino)methyl)benzonitrile

HRID 517586Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][N:4]1[C:8](=[O:9])/[C:7](=[CH:10]/[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH3:19])=[CH:13][CH:12]=2)/[S:6][C:5]1=[O:20].[C:21]([C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=1)#[N:22].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(OC1C=CC(/C=C2/C(=O)N(CCNC)C(=O)S/2)=CC=1)C>>[CH2:18]([O:17][C:14]1[CH:15]=[CH:16][C:11](/[CH:10]=[C:7]2/[C:8](=[O:9])[N:4]([CH2:3][CH2:2][NH:1][CH2:27][C:26]3[CH:29]=[CH:30][C:23]([C:21]#[N:22])=[CH:24][CH:25]=3)[C:5](=[O:20])[S:6]/2)=[CH:12][CH:13]=1)[CH3:19]

Participants

Reactant 4

HCID 660424-Cyanobenzaldehyde

HCID 1249836(Z)-3-(2-aminoethyl)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione

HCID 5049666Sodium triacetoxyborohydride

HCID 71697257(Z)-5-(4-ethoxybenzylidene)-3-(2-(methylamino)ethyl)thiazolidine-2,4-dione

Product 1

HCID 71697349(Z)-4-(((2-(5-(4-ethoxybenzylidene)-2,4-dioxothiazolidin-3-yl)ethyl)amino)methyl)benzonitrile

Procedure

The title compound 23e was prepared from compound 76 (146 mg, 0.50 mmol), 4-cyanobenzaldehyde (37 μL, 0.50 mmol) and sodium triacetoxyborohydride (318 mg, 1.50 mmol) in a manner similar to that described for 23a in 69.0% (140 mg) yield as a light-yellow solid.

Workup

customyield as a light-yellow solid

Sources & evidence

ORD record: ord-bc1099a8ec224d39adb47a2154c4cd44
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115122B2

Reaction notes

Loading…