1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 9805501, compound

HRID 1634136Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[C:12]1[NH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][C:17]([Cl:21])=[C:16]([Cl:22])[CH:15]=2)[C:6](O)=[O:7].CCN=C=NCCCN(C)C.C1C=NC2N(O)N=NC=2C=1.[NH2:44][CH:45]1[CH2:50][C:49]([CH3:52])([CH3:51])[N:48]([CH3:53])[C:47]([CH3:55])([CH3:54])[CH2:46]1>CN(C=O)C.O>[Cl:21][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][C:16]=1[Cl:22])[NH:13][C:12]([C:11]1[CH:10]=[CH:9][C:5]([C:6]([NH:44][CH:45]3[CH2:46][C:47]([CH3:54])([CH3:55])[N:48]([CH3:53])[C:49]([CH3:52])([CH3:51])[CH2:50]3)=[O:7])=[CH:4][C:3]=1[O:2][CH3:1])=[CH:20]2

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 3-methoxy-4-(5,6-dichloro-1H-indol-2-yl)-benzoic acid (0.15 g, 0.45 mmol), WSC (0.094 g, 0.5 mmol), HOAT (0.067 g, 0.5 mmol), 4-amino-1,2,2,6,6-pentamethylpiperidine (0.15 g, 0.9 mmol) in DMF (2 ml) was stirred at 50° C. for 18 h. The mixture was then poured in a large volume of water and extracted with AcOEt. The organic phase was washed with water, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (SiO2; CH2Cl2—MeOH—NH4OH: 91.5-7.5-1) then crystallised in di-isopropyl ether to afford 0.13 g (0.26 mmol. yield 59%) of the title compound, mp=260° C.

Workup

extractionextracted with AcOEt
washThe organic phase was washed with water
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography (SiO2; CH2Cl2—MeOH—NH4OH: 91.5-7.5-1)
customthen crystallised in di-isopropyl ether

Sources & evidence

ORD record: ord-43acdef04ae544be90f9dfcb23a22907
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06506758B2

Reaction notes

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