3,5-Dibromo-1-methyl-1H-pyrazin-2-one → tert-Butyl 5-(6-Bromo-4-methyl-3-oxo-3,4-dihydropyrazin-2-ylamino)isoindoline-2-carboxylate

HRID 1919028Notes

Reaction equation

HRID 1919028 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17]C[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH:18][C:19]3[C:24](=[O:25])[N:23]([CH3:26])[CH:22]=[C:21](C4C=C(F)C=C(N5CCN6C7CCCCC=7C=C6C5=O)C=4COC(=O)C)[N:20]=3)[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].NC1C=C2C(=CC=1)CN(C(OC(C)(C)C)=O)C2.[Br:70]C1C(=O)N(C)C=C(Br)N=1>>[Br:70][C:21]1[N:20]=[C:19]([NH:18][C:13]2[CH:12]=[C:11]3[C:10](=[CH:15][CH:14]=2)[CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:17]3)[C:24](=[O:25])[N:23]([CH3:26])[CH:22]=1

Participants

4

Reactant 3

HCID 130629693,5-Dibromo-1-methyl-1H-pyrazin-2-oneHCID 22591361tert-butyl 5-amino-2,3-dihydro-1H-isoindole-2-carboxylateHCID 67016272tert-Butyl-6-(6-(2-(acetoxymethyl)-5-fluoro-3-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)phenyl)-4-methyl-3-oxo-3,4-dihydropyrazin-2-ylamino)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 58044192tert-Butyl 5-(6-Bromo-4-methyl-3-oxo-3,4-dihydropyrazin-2-ylamino)isoindoline-2-carboxylate

Procedure

Following the procedures as described for 129a and starting with 600 mg of tert-butyl 5-aminoisoindoline-2-carboxylate (231c) and 685 mg of 3,5-dibromo-1-methylpyrazin-2(1H)-one, 231d was obtained as a yellow solid (732 mg, 68%). MS: [M+H]+ 421.

Sources & evidence

ORD record
ord-311fe610ddf3420ba7b6dfdbac3eef78
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

Loading…