3-(Isocyanomethyl)-5-(propan-2-yl)-1,2,4-oxadiazole → 7-Fluoro-4,5-dihydro-4,4-dimethyl-3-(5-isopropyl-1,2,4-oxadiazol-3-yl)-5-[(pyrrolidino)carbonyl]imidazo[1,5-a]quinoxaline

HRID 1378747Notes

Reaction equation

HRID 1378747 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=O)[C:6]([CH3:14])([CH3:13])[N:5]2[C:15]([N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:16].[N+:22]([CH2:24][C:25]1[N:29]=[C:28]([CH:30]([CH3:32])[CH3:31])[O:27][N:26]=1)#[C-:23]>>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH:23]=[N:22][C:24]([C:25]3[N:29]=[C:28]([CH:30]([CH3:32])[CH3:31])[O:27][N:26]=3)=[C:7]1[C:6]([CH3:14])([CH3:13])[N:5]2[C:15]([N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:16]

Participants

3

Reactant 2

HCID 106069203-(Isocyanomethyl)-5-(propan-2-yl)-1,2,4-oxadiazoleHCID 153912706-Fluoro-1,2,3,4-tetrahydro-3,3-dimethyl-4-[(pyrrolidino)carbonyl]quinoxalin-2-one

Product 1

HCID 536712787-Fluoro-4,5-dihydro-4,4-dimethyl-3-(5-isopropyl-1,2,4-oxadiazol-3-yl)-5-[(pyrrolidino)carbonyl]imidazo[1,5-a]quinoxaline

Procedure

Following the general procedure for EXAMPLE 30 and making non-critical variation but starting with 6-fluoro-1,2,3,4-tetrahydro-3,3-dimethyl-4-[(pyrrolidino)carbonyl]quinoxalin-2-one (XXXII, EXAMPLE 32, 0.647 g) and 3-isocyanomethyl-5-isopropyl-1,2,4-oxadiazole (0.403 g) the title compound is obtained which is crystallized from methylene chloride/ethyl ether/hexane, mp 154.5°-155.5°; MS (m/z) at 424; IR (mineral oil) 1527, 1657, 1414, 1172 and 1395 cm-1 ; NMR (CDCl3) 1.45, 1.7-2.0, 3.0, 3.3, 3.33, 3.58, 6.55, 6.74, 7.45 and 8.06 δ.

Sources & evidence

ORD record
ord-f67263c837c14899b3e255531c5b8acb
Source dataset
uspto-grants-1997_09
Patent number
US05668282

Reaction notes

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