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Acetic Acid → 2-(4-Chloro-2-oxo-1,2-dihydro-pyridin-3-yl)-6-(2-dimethylamino-1-methyl-ethyl)-1H-1,3,6-triaza-s-indacene-5,7-dione

HRID 2361189
ノート
印刷プレビュー

反応式

HRID 2361189 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-])=O)[C:7](=[O:14])[N:6]([CH:15]([CH3:20])[CH2:16][N:17]([CH3:19])[CH3:18])[C:5]2=[O:21].[CH3:22][C:23](O)=O.[ClH:26].[CH3:27][OH:28]>O1CCOCC1.O.[Pd]>[Cl:26][C:9]1[CH:10]=[CH:2][NH:1][C:27](=[O:28])[C:23]=1[C:22]1[NH:1][C:2]2[C:10]([N:11]=1)=[CH:9][C:8]1[C:7](=[O:14])[N:6]([CH:15]([CH3:20])[CH2:16][N:17]([CH3:19])[CH3:18])[C:5](=[O:21])[C:4]=1[CH:3]=2
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 887MethanolHCID 667934325-Amino-2-(2-dimethylamino-1-methyl-ethyl)-6-nitro-isoindole-1,3-dione

生成物 1

HCID 1363511972-(4-Chloro-2-oxo-1,2-dihydro-pyridin-3-yl)-6-(2-dimethylamino-1-methyl-ethyl)-1H-1,3,6-triaza-s-indacene-5,7-dione収率 80%

試薬・触媒・溶媒 3

HCID 23938
Palladium
触媒
HCID 962Water溶媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
70 °C

実験手順

The mixture of 5-amino-2-(2-dimethylamino-1-methyl-ethyl)-6-nitro-isoindole-1,3-dione (585 mg, 2.0 mmol) and Pd/C (60 mg) in MeOH (95 mL) was stirred under atmospheric H2 for 2.5 h and filtered through Celite. The filtrate was mixed with 4-chloro-2-methoxynicotinic aldehyde (343.2 mg, 2.0 mmol) and HOAc (5 mL), stirred at the room temperature for 62 h, and evaporated under reduced pressure to afford an oil crude which was mixed with HCl in dioxane (4 M, 25 mL) and H2O (2 mL), heated at 70° C. for 1 h and evaporated. The residue was diluted with a mixed solvent of MeOH/DCM (50 mL/50 mL), basified with 28% aqueous NH4OH, and concentrated. Chromatography of the residue with CH2Cl2/MeOH/28% aqueous NH4OH (60:10:1) afforded the title compound (642 mg, 80%). 1H NMR (DMSO-d6) δ 1.39 (d, J=6 Hz, 3H, CH3), 2.14 (s, 6H, 2CH3), 2.29 (m, 1H), 3.04 (m, 1H), 4.40 (m, 1H), 6.59 (d, J=8 Hz, 1H), 7.69 (d, J=8 Hz, 1H), 8.04 (s, 1H), 8.05 (s, 1H); ESI-MS m/z 400.3 (MH+).

後処理

  1. filtrationfiltered through Celite
  2. stirringstirred at the room temperature for 62 h
  3. customevaporated under reduced pressure
  4. customto afford an oil crude which
  5. customevaporated
  6. additionThe residue was diluted with a mixed solvent of MeOH/DCM (50 mL/50 mL)
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-3f54678abe3044c5a34fcbc6398ba7fc
出典データセット
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08686005B2

反応ノート

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