Morpholine → HCID 21956445, compound

HRID 2213746Notes

Reaction equation

HRID 2213746 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:14][C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=3)=[C:7]([C:12]#[N:13])[CH:8]=[N:9]2)=[CH:4][C:3]=1[NH:27][C:28](=[O:31])[CH:29]=[CH2:30].NC1C=C2C(=CC=1NC(=O)C=C)N=CC(C#N)=C2NC1C=C(OC)C(OC)=C(OC)C=1.[NH:63]1[CH2:68][CH2:67][O:66][CH2:65][CH2:64]1>CN(C)C=O>[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:14][C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=3)=[C:7]([C:12]#[N:13])[CH:8]=[N:9]2)=[CH:4][C:3]=1[NH:27][C:28](=[O:31])[CH2:29][CH2:30][N:63]1[CH2:68][CH2:67][O:66][CH2:65][CH2:64]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 21956481HCID 21956481, compoundHCID 21956491HCID 21956491, compound

Product 1

HCID 21956445HCID 21956445, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.025 g (0.06 mmol) of N-[7-amino-3-cyano-4-(3,4,5-trimethoxyanilino)-6-quinolinyl]acrylamide and N-[6-amino-3-cyano-4-(3,4,5-trimethoxyanilino)-7-quinolinyl]acrylamide and 0.05 mL (6.0 mmol) of morpholine in 0.2 mL of N,N-dimethylformamide is stirred at room temperature overnight and the solvent is evaporated to dryness to yield an oil. The oil is triturated with diethyl ether several times and dried to yield 0.03 g of N-[7-amino-3-cyano-4-(3,4,5-trimethoxyanilino)-6-quinolinyl]-3-(4-morpholinyl)propanamide and N-[6-amino-3-cyano-4-(3,4,5-trimethoxyanilino)-7-quinolinyl]-3-(4-morpholinyl)propanamide as a yellow solid.

Workup

  1. customthe solvent is evaporated to dryness
  2. customto yield an oil
  3. customThe oil is triturated with diethyl ether several times
  4. customdried

Sources & evidence

ORD record
ord-927f40a2840f4411bda1dd4478b02c02
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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