2-Aminopyridine → HCID 44517258, compound

HRID 43119Notes

Reaction equation

HRID 43119 reaction equation
[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([F:12])[C:3]=1[C:13]1[C:22]2[N:21]=[CH:20][CH:19]=[N:18][C:17]=2[C:16]([C:23](O)=[O:24])=[CH:15][CH:14]=1.[NH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1>>[N:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[NH:26][C:23]([C:16]1[C:17]2[N:18]=[CH:19][CH:20]=[N:21][C:22]=2[C:13]([C:3]2[C:2]([F:1])=[C:7]([O:8][CH3:9])[CH:6]=[C:5]([O:10][CH3:11])[C:4]=2[F:12])=[CH:14][CH:15]=1)=[O:24]

Participants

3

Reactant 2

HCID 104392-AminopyridineHCID 592928348-(2,6-Difluoro-3,5-dimethoxy-phenyl)quinoxaline-5-carboxylic acid

Product 1

HCID 44517258HCID 44517258, compound

Procedure

The title compound was prepared in analogy to the procedure described in Step 14.1 but using 8-(2,6-difluoro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid (Step 88.1), 2-aminopyridine, and stirring the reaction mixture for 72 h at rt. The crude product was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 96:3:1), followed by trituration in Et2O, a second silica gel column chromatography (Hex/EtOAc, 1:4) and an additional trituration in Et2O. Title compound: ESI-MS: 423.1 [M+H]+; tR=4.21 min (System 1); TLC: Rf=0.19 (Hex/EtOAc, 1:4).

Workup

  1. customThe crude product was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 96:3:1)

Sources & evidence

ORD record
ord-840ecc9337674b2fa7720a9be16f1c78
Source dataset
uspto-grants-2013_09
Patent number
US08536175B2

Reaction notes

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