Morpholine → HCID 178522099, compound

HRID 2109029

Reaction equation

HRID 2109029 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[O:19][C:18]3[C:13](=[N:14][C:15]([C:20]([OH:22])=O)=[CH:16][CH:17]=3)[C:12]=2[NH:23][C:24]([C@H:26]2[CH2:31][CH2:30][C@H:29]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][C:33]3=[O:38])[CH2:28][CH2:27]2)=[O:25])=[O:10])=[N:6][CH:7]=1.[NH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.C(OCC)(=O)C.O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[O:19][C:18]3[C:13](=[N:14][C:15]([C:20]([N:39]4[CH2:44][CH2:43][O:42][CH2:41][CH2:40]4)=[O:22])=[CH:16][CH:17]=3)[C:12]=2[NH:23][C:24]([C@H:26]2[CH2:27][CH2:28][C@H:29]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][C:33]3=[O:38])[CH2:30][CH2:31]2)=[O:25])=[O:10])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178524191HCID 178524191, compound

Product 1

HCID 178522099HCID 178522099, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21939870Tetrahydrofuran ethyl acetateSolvent

Procedure

2-{[(5-Chloropyridin-2-yl)amino]carbonyl}-3-({[trans-4-(3-oxomorpholin-4-yl)cyclohexyl]carbonyl}amino)furo[3,2-b]pyridine-5-carboxylic acid (100 mg) obtained in Example 79 is dissolved in N,N-dimethylformamide (3 ml), and thereto are added successively morpholine (32 μl), 1-hydroxybenzotriazole (50 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (71 mg), and the mixture is stirred at room temperature for 15 hours. The reaction solution is diluted with ethyl acetate-tetrahydrofuran, and the solution is washed successively with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over sodium sulfate. The solvent is evaporated under reduced pressure and the resulting residue is suspended in ethyl acetate-diethyl ether. The solid precipitates are collected by filtration to give the title compound (109 mg).

Workup

  1. washthe solution is washed successively with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
  2. dry with materialdried over sodium sulfate
  3. customThe solvent is evaporated under reduced pressure
  4. customThe solid precipitates
  5. filtrationare collected by filtration

Sources & evidence

ORD record
ord-3155bfcf6f054db7b017720da0154575
Source dataset
uspto-grants-2009_04
Patent number
US07514449B2

Linked notes

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