Morpholine → HCID 21956445, compound

HRID 989312Notes

Reaction equation

HRID 989312 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-1fad676f940a42a9b83c6d93a46bb57d
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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