1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86668199, compound

HRID 1623670Notes

Reaction equation

HRID 1623670 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[NH2:19][C:20]1[CH:21]=[C:22]([CH2:26][C:27]([O:29][CH3:30])=[O:28])[CH:23]=[CH:24][CH:25]=1.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:6]([C:7]([NH:19][C:20]2[CH:21]=[C:22]([CH2:26][C:27]([O:29][CH3:30])=[O:28])[CH:23]=[CH:24][CH:25]=2)=[O:9])[CH:10]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 33011592-(benzyloxy)-5-chlorobenzoic acidHCID 13054266Methyl 3-aminophenylacetate

Product 1

HCID 86668199HCID 86668199, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-chloro-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 45; 50 mg, 0.19 mmol), methyl (3-aminophenyl)acetate (may be prepared as described in Description 44; 48 mg, 0.29 mmol), EDAC (56 mg, 0.29 mmol), and dichloromethane (3 ml) was heated in the microwave at 60° C. for 40 minutes. DIPEA (53 μl, 0.3 mmol) was added and the mixture was heated at 60° C. in the microwave for another 20 minutes. The reaction mixture was purified by SCX cartridge, eluting with methanol. The fractions were combined and evaporated to give the title compound as an off-white solid. 35 mg.

Workup

  1. temperaturethe mixture was heated at 60° C. in the microwave for another 20 minutes
  2. customThe reaction mixture was purified by SCX cartridge
  3. washeluting with methanol
  4. customevaporated

Sources & evidence

ORD record
ord-53b93fc6fb1e4471837822d1f11d4c2c
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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