1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59846223, compound

HRID 1697075Notes

Reaction equation

HRID 1697075 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:20])/[CH:9]=[CH:10]/[C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=2)=[C:4]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:3]=1.[NH2:28][CH:29]1[CH2:34][CH2:33][CH:32]([OH:35])[CH2:31][CH2:30]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:20])/[CH:9]=[CH:10]/[C:11]2[CH:12]=[CH:13][C:14]([C:15]([NH:28][CH:29]3[CH2:34][CH2:33][CH:32]([OH:35])[CH2:31][CH2:30]3)=[O:17])=[CH:18][CH:19]=2)=[C:4]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:3]=1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 812934-AminocyclohexanolHCID 81531DiisopropylethylamineHCID 59846266HCID 59846266, compound

Product 1

HCID 59846223HCID 59846223, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-[(E)-3-(4-chloro-2-phenylamino-phenyl)-3-oxo-propenyl]-benzoic acid (0.2 g, 0.53 mmol), 4-amino-cyclohexanol (61 mg, 0.53 mmol), EDCI (152 mg, 0.8 mmol), HOBt (25 mg), DIPEA (1 mL) in THF (50 mL) was stirred at RT overnight. The resulting mixture was evaporated under reduced pressure, and the residue partitioned between water and EtOAc. The resulting precipitate was collected by filtration and dried in a vacuum oven, the filtrate separated, the organic layer dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by preparative TLC (EtOAc/hexane, 75:25) and combined with the solid collected to yield 4-[(E)-3-(4-chloro-2-phenylamino-phenyl)-3-oxo-propenyl]-N-(4-hydroxy-cyclohexyl)-benzamide (197 mg). MS=475 [M+H]+.

Workup

  1. customThe resulting mixture was evaporated under reduced pressure
  2. customthe residue partitioned between water and EtOAc
  3. filtrationThe resulting precipitate was collected by filtration
  4. customdried in a vacuum oven
  5. customthe filtrate separated
  6. dry with materialthe organic layer dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe residue was purified by preparative TLC (EtOAc/hexane, 75:25)
  10. customcollected

Sources & evidence

ORD record
ord-6be78dc8698a46b49d43b691430057fe
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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