4-Methylmorpholine → HCID 86604652, compound

HRID 347433Notes

Reaction equation

HRID 347433 reaction equation
Cl.CN(C)CCCN=C=NCC.[C:13]([C:15]1[CH:16]=[N:17][C:18]2[C:23]([C:24]=1[NH:25][C:26]1[CH:31]=[CH:30][C:29](/[CH:32]=[CH:33]/[C:34]([OH:36])=O)=[C:28]3[O:37][CH2:38][O:39][C:27]=13)=[CH:22][C:21]([O:40][CH3:41])=[C:20]([O:42][CH3:43])[CH:19]=2)#[N:14].[NH:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1.CN1CCOCC1.ON1C2C=CC=CC=2N=N1>C(Cl)Cl.CN(C=O)C>[C:13]([C:15]1[CH:16]=[N:17][C:18]2[C:23]([C:24]=1[NH:25][C:26]1[CH:31]=[CH:30][C:29](/[CH:32]=[CH:33]/[C:34]([N:44]3[CH2:49][CH2:48][O:47][CH2:46][CH2:45]3)=[O:36])=[C:28]3[O:37][CH2:38][O:39][C:27]=13)=[CH:22][C:21]([O:40][CH3:41])=[C:20]([O:42][CH3:43])[CH:19]=2)#[N:14]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 8083MorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21082674HCID 21082674, compound

Product 1

HCID 86604652HCID 86604652, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.196 g) was added to a mixture of (2E)-3-[4-(3-cyano-6,7-dimethoxyquinolin-4-ylamino)-2,3-methylenedioxyphenyl]acrylic acid (0.35 g), morpholine (0.36 ml), N-methylmorpholine (0.112 ml), 1-hydroxybenzotriazole (0.112 ml), DMF (2 ml) and methylene chloride (10 ml) and the reaction mixture was stirred at ambient temperature for 12 hours. The resultant mixture was partitioned between methylene chloride and water. The organic layer was dried over magnesium sulphate and evaporated and the residue was purified by column chromatography on silica using increasingly polar mixtures of methylene chloride and methanol as eluent. The material so obtained was triturated under diethyl ether. There was thus obtained the title compound as a solid (0.031 g); NMR Spectrum: (DMSOd6) 3.66 (s, 8H), 3.96 (s, 6H), 6.09 (s, 2H), 6.87 (d, 1H), 7.19 (d, 1H), 7.28 (d, 1H), 7.34 (s, 1H), 7.49 (d, 1H), 7.77 (s, 1H), 8.48 (s, 1H), 9.63 (s, 1H); Mass Spectrum: M+H+ 489.

Workup

  1. customThe resultant mixture was partitioned between methylene chloride and water
  2. dry with materialThe organic layer was dried over magnesium sulphate
  3. customevaporated
  4. customthe residue was purified by column chromatography on silica using
  5. temperatureincreasingly polar mixtures of methylene chloride and methanol as eluent
  6. customThe material so obtained
  7. customwas triturated under diethyl ether

Sources & evidence

ORD record
ord-ac59ed2c31f446a4ba44e9e4653f03d9
Source dataset
uspto-grants-2007_02
Patent number
US07173135B2

Reaction notes

Loading…