Dimethylformamide → 4-(Aminocarbonyl)benzoic acid, 4-(4-((6-chloro-2-quin-oxalinyl)oxy)phenoxy)-2-pentenyl ester

HRID 569008Notes

Reaction equation

HRID 569008 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][C:13]1[CH:25]=[CH:24][C:16]([O:17][CH:18]([CH3:23])[CH:19]=[CH:20][CH2:21][OH:22])=[CH:15][CH:14]=1)[CH:6]=[N:5]2.[NH2:26][C:27]([C:29]1[CH:37]=[CH:36][C:32]([C:33](O)=[O:34])=[CH:31][CH:30]=1)=[O:28].C1(N=C=NC2CCCCC2)CCCCC1.CN(C=O)C>CN(C)C1C=CN=CC=1.O.CCOCC>[NH2:26][C:27]([C:29]1[CH:37]=[CH:36][C:32]([C:33]([O:22][CH2:21][CH:20]=[CH:19][CH:18]([O:17][C:16]2[CH:15]=[CH:14][C:13]([O:12][C:7]3[CH:6]=[N:5][C:4]4[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=4)[N:8]=3)=[CH:25][CH:24]=2)[CH3:23])=[O:34])=[CH:31][CH:30]=1)=[O:28]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 10868Dicyclohexylcarbodiimide2×HCID 5060574-Carbamoylbenzoic acid2×HCID 542751324-(4-((6-Chloro-2-quinoxalinyl)oxy)phenoxy)2-penten-1-ol

Product 1

HCID 569955344-(Aminocarbonyl)benzoic acid, 4-(4-((6-chloro-2-quin-oxalinyl)oxy)phenoxy)-2-pentenyl esterYield 26%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1.5 g (4.2 mmol) of the pentenol obtained in Example 3 above, 1.04 g (6.3 mmol) of 4-(aminocarbonyl)benzoic acid, 1.30 g (6.3 mmol) of dicyclohexylcarbodiimide (DDC), 0.05 g of 4-(dimethylamino)pyridine and 20 ml of DMF was stirred at room temperature overnight. An additional 0.3 g of DCC and 0.25 g of 4-(aminocarbonyl)benzoic acid were added and the mixture was stirred an additional 20 hours. The mixture was then poured into ether, water added and filtered. The filtrates were separated, and the organic layer washed with saturated aqueous NaHCO3 and water, dried over MgSO4 and evaporated to dryness. The residue was purified by preparative scale HPLC, eluting with a 3:2 hexane:acetone mixture to give 0.55 g of the desired product as a tan, glassy solid, m.p. 144°-148° C. (Compound 29).

Workup

  1. stirringthe mixture was stirred an additional 20 hours
  2. additionadded
  3. filtrationfiltered
  4. customThe filtrates were separated
  5. washthe organic layer washed with saturated aqueous NaHCO3 and water
  6. dry with materialdried over MgSO4
  7. customevaporated to dryness
  8. customThe residue was purified by preparative scale HPLC
  9. washeluting with a 3:2 hexane

Sources & evidence

ORD record
ord-b14a26c24dee4b8a997fb67fed5e7b8d
Source dataset
uspto-grants-1988_03
Patent number
US04731108

Reaction notes

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