2,4-Dimethoxyaniline → HCID 86706291, compound

HRID 2205878Notes

Reaction equation

HRID 2205878 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[C:9]([C:18]3[CH:19]=[N:20][N:21]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:22]=3)[N:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:4]=2[CH:3]=1.[CH3:30][O:31][C:32]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:33]=1[NH2:40]>>[C:26]([O:25][C:23]([N:21]1[CH:22]=[C:18]([C:9]2[N:10]([C:11]([O:13][C:14]([CH3:16])([CH3:15])[CH3:17])=[O:12])[C:4]3[CH:3]=[C:2]([NH:40][C:33]4[CH:34]=[CH:35][C:36]([O:38][CH3:39])=[CH:37][C:32]=4[O:31][CH3:30])[N:7]=[CH:6][C:5]=3[CH:8]=2)[CH:19]=[N:20]1)=[O:24])([CH3:27])([CH3:29])[CH3:28]

Participants

3

Reactant 2

HCID 176522,4-DimethoxyanilineHCID 86706270HCID 86706270, compound

Product 1

HCID 86706291HCID 86706291, compoundYield 53%

Procedure

The title compound was prepared in 53% yield from compound (10) and 2,4-dimethoxyphenylamine using the method described for Preparation 35. 1H-NMR (CDCl3, 500 MHz): δ 1.50 (s, 9H), 1.69 (s, 9H), 3.83 (s, 3H), 3.87 (s, 3H), 6.52 (dd, J=2.52, 8.51 Hz, 1H), 6.56 (d, J=0.95 Hz, 1H), 6.57 (d, J=2.52 Hz, 1H), 6.66 (br s, 1H, NH), 7.43 (m, 1H), 7.67 (d, J=8.83 Hz, 1H), 7.82 (m, 1H), 8.20 (d, J=0.95 Hz, 1H), 8.43 (d, J=0.95 Hz, 1H).

Workup

  1. customdescribed for Preparation 35

Sources & evidence

ORD record
ord-db5e28d9f6a944cab20bd29957fbe24d
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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