Dicyclohexylcarbodiimide → HCID 54710175, compound

HRID 1080645Notes

Reaction equation

HRID 1080645 reaction equation
[C:1]([C:4]1[C:16](=[O:17])[N:12]2[CH2:13][CH2:14][O:15][C:10]3[C:11]2=[C:6]([CH:7]=[C:8]([O:18][CH3:19])[CH:9]=3)[C:5]=1[OH:20])([OH:3])=O.[CH2:21]([O:23][C:24]([CH:26]1[CH2:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[NH:27]1)=[O:25])[CH3:22].C1(N=C=NC2CCCCC2)CCCCC1>C1(C)C=CC=CC=1>[CH2:21]([O:23][C:24]([CH:26]1[CH2:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]1[C:1]([C:4]1[C:16](=[O:17])[N:12]2[CH2:13][CH2:14][O:15][C:10]3[C:11]2=[C:6]([CH:7]=[C:8]([O:18][CH3:19])[CH:9]=3)[C:5]=1[OH:20])=[O:3])=[O:25])[CH3:22]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 11949691Ethyl Indoline-2-carboxylateHCID 54710190HCID 54710190, compound

Product 1

HCID 54710175HCID 54710175, compoundYield 114.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6-carboxy-2,3-dihydro-7-hydroxy-9-methoxy-5-oxo-5H-pyrido[1,2,3-de]-1,4-benzoxazine (1.5 g), 2-ethoxycarbonylindoline (2.3 g) and 1,3-dicyclohexylcarbodiimide (3 g) in toluene (20 ml) was stirred at 90° C. for 3 hours. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with chloroform-methanol (30:1) to give 2,3-dihydro-6-(2-ethoxycarbonyl-1-indolinylcarbonyl)-7-hydroxy-9-methoxy-5-oxo-5H-pyrido[1,2,3-de]-1,4-benzoxazine (2.8 g).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel eluting with chloroform-methanol (30:1)

Sources & evidence

ORD record
ord-df49eac1d7554c7097bfbd53bd6c370b
Source dataset
uspto-grants-1996_12
Patent number
US05583135

Reaction notes

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