Water → HCID 53748226, compound

HRID 1934971Notes

Reaction equation

HRID 1934971 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[Br:6][C:7]1[CH:8]=[C:9]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([NH:24][C:25](=[O:30])[CH:26]=[CH:27][CH2:28]Br)[CH:22]=3)[N:17]=[CH:16][C:15]=2[C:31]#[N:32])[CH:10]=[CH:11][CH:12]=1.O.C(OCC)(=O)C>O1CCCC1.CN(C)C=O>[Br:6][C:7]1[CH:8]=[C:9]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([NH:24][C:25](=[O:30])[CH:26]=[CH:27][CH2:28][N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[CH:22]=3)[N:17]=[CH:16][C:15]=2[C:31]#[N:32])[CH:10]=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8021DiethylamineHCID 8857Ethyl AcetateHCID 54059945HCID 54059945, compound

Product 1

HCID 53748226HCID 53748226, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3.15 ml (30 mmoles) of diethylamine in 15 ml of tetrahydrofuran was cooled in an ice bath and a solution of 729 mg (1.5 mmoles) of 4-bromo-but-2-enoic acid[4-(3-bromo-phenylamino)-3-cyano-quinolin-6-yl]-amide in 5 ml of N,N-dimethylformamide was added dropwise. Stirring and cooling were continued for 2 hours. Then 25 ml of water and 15 ml of ethyl acetate were added. The layers were separated and aqueous layer was extracted with 2-15 ml portions of 1:1 tetrahydrofuran-ethyl acetate. The combined organic layers were absorbed onto silica gel and chromatographed on silica gel. The column was eluted with a gradient of 1:19 to 1:4 methanol-methylene chloride to give 367 mg (51%) of 4-Diethylamino-but-2-enoic acid[4-(3-bromo-phenylamino)-3-cyano-quinolin-6-yl]-amide. The compound melted at 141-145 deg: mass spectrum (electrospray, m/e): M+H 478.0, 480.0.

Workup

  1. temperaturecooling
  2. customThe layers were separated
  3. extractionaqueous layer was extracted with 2-15 ml portions of 1:1 tetrahydrofuran-ethyl acetate
  4. customThe combined organic layers were absorbed onto silica gel
  5. customchromatographed on silica gel
  6. washThe column was eluted with a gradient of 1:19 to 1:4 methanol-methylene chloride

Sources & evidence

ORD record
ord-2bd11eae41364460a72b8ef9042978cf
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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