1,4-Dioxane → HCID 67314675, compound

HRID 1011399Notes

Reaction equation

HRID 1011399 reaction equation
[N:1]1([CH2:7][CH2:8][NH2:9])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl[C:11]1[N:16]=[CH:15][C:14]2[C:17](=[C:22]3[C:30]4[C:25](=[CH:26][CH:27]=[C:28]([F:31])[CH:29]=4)[NH:24][C:23]3=[O:32])[O:18][CH:19]([CH2:20][CH3:21])[C:13]=2[C:12]=1[Cl:33].O1CCOC[CH2:35]1>>[Cl:33][C:12]1[C:13]2[CH:19]([CH2:20][CH2:21][CH3:35])[O:18][C:17](=[C:22]3[C:30]4[C:25](=[CH:26][CH:27]=[C:28]([F:31])[CH:29]=4)[NH:24][C:23]3=[O:32])[C:14]=2[CH:15]=[N:16][C:11]=1[NH:9][CH2:8][CH2:7][N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 312751,4-DioxaneHCID 4082852-MorpholinoethylamineHCID 76798889HCID 76798889, compound

Product 1

HCID 67314675HCID 67314675, compoundYield 24%

Conditions

Temperature
100 °C

Procedure

A solution of 2-morpholin-4-yl-ethylamine (320 mg, 2.45 mmol) in 3 mL of dioxane is treated with 3-(6,7-dichloro-1-ethyl-1H-furo[3,4-c]pyridin-3-ylidene)-5-fluoro-1,3-dihydro-indol-2-one (100 mg, 0.26 mmol) in one portion and the reaction mixture is heated to 100° C. overnight. The reaction mixture is concentrated and the residue is purified by chromatography (silica gel, 5% MeOH/EtOAc). The product containing fractions are concentrated to give the title compound as a yellow solid (29 mg, 24%).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customthe residue is purified by chromatography (silica gel, 5% MeOH/EtOAc)
  3. additionThe product containing fractions
  4. concentrationare concentrated

Sources & evidence

ORD record
ord-e2cb6f7746104f7d9c1f53bd39b04b9e
Source dataset
uspto-grants-2011_07
Patent number
US07977351B2

Reaction notes

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