3-(Isocyanomethyl)-5-(propan-2-yl)-1,2,4-oxadiazole → 6-Fluoro-4,5-dihydro-3-(5-isopropyl-1,2,4-oxadiazol-3-yl)-5-[(pyrrolidino)carbonyl]imidazo[1,5-a]quinoxaline

HRID 1378745Notes

Reaction equation

HRID 1378745 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]([C:13]([N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:14])[CH2:5][C:6](=O)[NH:7]2.[N+:20]([CH2:22][C:23]1[N:27]=[C:26]([CH:28]([CH3:30])[CH3:29])[O:25][N:24]=1)#[C-:21]>>[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]([C:13]([N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:14])[CH2:5][C:6]1[N:7]2[CH:21]=[N:20][C:22]=1[C:23]1[N:27]=[C:26]([CH:28]([CH3:30])[CH3:29])[O:25][N:24]=1

Participants

3

Reactant 2

HCID 106069203-(Isocyanomethyl)-5-(propan-2-yl)-1,2,4-oxadiazoleHCID 229128415-Fluoro-1,2,3,4-tetrahydro4-[(pyrrolidino)carbonyl]quinoxalin-2-one

Product 1

HCID 229129266-Fluoro-4,5-dihydro-3-(5-isopropyl-1,2,4-oxadiazol-3-yl)-5-[(pyrrolidino)carbonyl]imidazo[1,5-a]quinoxaline

Procedure

Following the general procedure of EXAMPLE 30 and making non-critical variations but using 5-fluoro-1,2,3,4-tetrahydro-4-[(pyrrolidino)carbonyl]quinoxalin-2-one (XXXII, EXAMPLE 29, 0.978 g) and 3-isocyanomethyl-5-isopropyl-1,2,4-oxadiazole (0.673 g) are converted to the title compound, mp 169°-170°; MS (m/z) at 396; IR (mineral oil) 1657, 1495, 1216, 1614 and 785 cm-1 ; NMR (CDCl3) 1.47, 1.86, 3.30, 3.34, 5.13, 7.08, 7.22, 7.38 and 8.12 δ.

Sources & evidence

ORD record
ord-42f91a800bac453e9af617a96a97c34d
Source dataset
uspto-grants-1997_09
Patent number
US05668282

Reaction notes

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