(2Z)-3-Amino-2-butenenitrile → HCID 135844978, compound

Reaction equation

[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([CH:12]=O)[C:10]=2[CH:11]=1.[CH3:14][C:15]1[N:16]=[C:17]([CH2:20][C:21]([CH3:23])=O)[S:18][CH:19]=1.[NH2:24]/[C:25](/[CH3:29])=[CH:26]\[C:27]#[N:28]>C(O)(C)C>[CH3:29][C:25]1[NH:24][C:21]([CH3:23])=[C:20]([C:17]2[S:18][CH:19]=[C:15]([CH3:14])[N:16]=2)[CH:12]([C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[C:10]=2[CH:11]=[C:2]([CH3:1])[CH:3]=[N:4]3)[C:26]=1[C:27]#[N:28]

Participants

Procedure

150 mg (0.876 mmol) of the compound from example 23A, 135 mg (0.876 mmol) of the compound from example 4A and 71 mg (0.876 mmol) of 3-aminocrotononitrile are dissolved in 4 ml of isopropanol and stirred at the reflux temperature overnight. After cooling to room temperature, the volatile components are removed in a rotary evaporator, and the crude product is purified by preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid, gradient 20:80→95:5). 145 mg (44% of theory) of the title compound are obtained.