tert-Butyl isocyanoacetate → tert-Butyl 7-fluoro-4,5-dihydro-4,4-dimethyl-5-[(pyrrolidino)-carbonyl]imidazo[1,5-a]quinoxaline-3-carboxylate

HRID 1736690Notes

Reaction equation

HRID 1736690 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]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])#[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]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[C:7]1[C:6]([CH3:13])([CH3:14])[N:5]2[C:15]([N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:16]

Participants

3

Reactant 2

HCID 2759404tert-Butyl isocyanoacetateHCID 153912706-Fluoro-1,2,3,4-tetrahydro-3,3-dimethyl-4-[(pyrrolidino)carbonyl]quinoxalin-2-one

Product 1

HCID 53869729tert-Butyl 7-fluoro-4,5-dihydro-4,4-dimethyl-5-[(pyrrolidino)-carbonyl]imidazo[1,5-a]quinoxaline-3-carboxylate

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, 0.750 g) and t-butyl isocyanoacetate (0.436 g) are converted to the title compound. After crystallization from ethyl ether/hexane, mp 168.5°-169.5°; MS (m/z) at 414; IR (mineral oil) 1713, 1668, 1520, 1181 and 1155 cm-1 ; NMR (CDCl3) 1.63, 1.8, 1.92, 2.08, 2.95, 3.23, 3.58, 6.52, 6.71 and 7.92 δ.

Sources & evidence

ORD record
ord-90a3bd1279bd4615b16096827d832b1a
Source dataset
uspto-grants-1996_07
Patent number
US05541324

Reaction notes

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