8-(2-Fluoro-3,5-dimethoxy-phenyl)quinoxaline-5-carboxylic acid → HCID 59292852, compound

HRID 2409685Notes

Reaction equation

HRID 2409685 reaction equation
[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[CH:4][C:3]=1[C:12]1[C:21]2[N:20]=[CH:19][CH:18]=[N:17][C:16]=2[C:15]([C:22](O)=[O:23])=[CH:14][CH:13]=1.[NH2:25][C:26]1[N:31]=[CH:30][C:29]([CH2:32][N:33]([CH3:39])[CH2:34][CH2:35][N:36]([CH3:38])[CH3:37])=[CH:28][CH:27]=1>>[CH3:37][N:36]([CH3:38])[CH2:35][CH2:34][N:33]([CH2:32][C:29]1[CH:28]=[CH:27][C:26]([NH:25][C:22]([C:15]2[C:16]3[N:17]=[CH:18][CH:19]=[N:20][C:21]=3[C:12]([C:3]3[CH:4]=[C:5]([O:10][CH3:11])[CH:6]=[C:7]([O:8][CH3:9])[C:2]=3[F:1])=[CH:13][CH:14]=2)=[O:23])=[N:31][CH:30]=1)[CH3:39]

Participants

3

Reactant 2

HCID 592928668-(2-Fluoro-3,5-dimethoxy-phenyl)quinoxaline-5-carboxylic acidHCID 592929455-({[2-(Dimethylamino)ethyl](methyl)amino}methyl)pyridin-2-amine

Product 1

HCID 59292852HCID 59292852, compound

Procedure

The title compound was prepared in analogy to the procedure described in Step 14.1 but using 8-(2-fluoro-3,5-dimethoxy-phenyl)-quinoxaline-5-carboxylic acid (Step 94.1), N-(6-amino-pyridin-3-ylmethyl)-N,N′,N′-trimethyl-ethane-1,2-diamine (prepared as described in Example 26 but using N,N,N′-trimethyl-ethane-1,2-diamine in Step 26.2) and stirring the reaction mixture for 18 h at rt. The crude product was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 94:5:1). Title compound: ESI-MS: 519.2 [M+H]+; tR=3.26 min (System 1); TLC: Rf=0.13 (DCM/MeOH/NH3aq, 94:5:1).

Workup

  1. customThe crude product was purified by silica gel column chromatography (DCM/MeOH/NH3aq, 94:5:1)

Sources & evidence

ORD record
ord-6044fa92eca748bd87045121e5cdaef3
Source dataset
uspto-grants-2014_08
Patent number
US08815901B2

Reaction notes

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