Ethyl isocyanate → HCID 58827101, compound

HRID 1877945Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH:10]1[N:14]2[CH:15]=[N:16][CH:17]=[C:13]2[CH2:12][CH2:11]1)[C:5]#[N:6].[CH2:18]([N:20]=[C:21]=[O:22])[CH3:19]>CN(C=O)C>[C:5]([C:4]1[CH:7]=[CH:8][C:9]([CH:10]2[N:14]3[CH:15]=[N:16][CH:17]=[C:13]3[CH2:12][CH2:11]2)=[C:2]([NH:1][C:21]([NH:20][CH2:18][CH3:19])=[O:22])[CH:3]=1)#[N:6]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 3-Amino-4-(6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)benzonitrile (0.090 g, 0.420 mmol), given as example 6B, and DMF (5 mL) is added ethylisocyanate (0.040 mL, 0.510 mmol). The solution is heated to 70° C. in a microwave reactor for 1.5 h followed by heating at 70° C. in an oil bath overnight. The solution is then concentrated and the residue purified via flash chromatography (1-10% MeOH/CH2Cl2) to give 1-[5-Cyano-2-(6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)phenyl]-3-ethylurea. MS (ESI) m/z 296.1 (M+H); 1H NMR (400 MHz, CDCl3) δ ppm 1.16 (t, J=7.2 Hz, 3 H), 2.47-2.62 (m, 1 H), 2.82-3.04 (m, 2 H), 3.05-3.17 (m, 1 H), 3.21-3.33 (m, 2 H), 5.63 (app t, J=6.8 Hz, 1 H), 5.80 (br s, 1 H), 6.82 (s, 1 H), 6.91 (d, J=8.1 Hz, 1 H), 7.30 (dd, J=8.1, 1.5 Hz, 1 H), 7.39 (s, 1 H), 7.53 (br s, 1 H), 7.97 (d, J=1.3 Hz, 1 H).

Workup

temperatureby heating at 70° C. in an oil bath overnight
concentrationThe solution is then concentrated
customthe residue purified via flash chromatography (1-10% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-58319ec52d4f4b0db3b08f06e53916a3
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314097B2

Reaction notes

Loading…