1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58674506, compound

HRID 1994146Notes

Reaction equation

HRID 1994146 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([O:15][C:16]2[CH:17]=[C:18]([CH2:22][CH2:23][C:24](O)=[O:25])[CH:19]=[CH:20][CH:21]=2)[CH:12]=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:27]([C:31]1[CH:32]=[C:33]([CH:35]=[CH:36][CH:37]=1)[NH2:34])([CH3:30])([CH3:29])[CH3:28].CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:27]([C:31]1[CH:32]=[C:33]([NH:34][C:24](=[O:25])[CH2:23][CH2:22][C:18]2[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=2)[O:15][C:13]2[CH:12]=[CH:11][N:10]=[C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH:14]=2)[CH:35]=[CH:36][CH:37]=1)([CH3:30])([CH3:28])[CH3:29]

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 793343-tert-ButylanilineHCID 58674369HCID 58674369, compound

Product 1

HCID 58674506HCID 58674506, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-[3-({2-[(tert-butoxycarbonyl)amino]pyridin-4-yl}oxy)phenyl]propanoic acid (333 mg, 0.93 mmol) in DCM (10 mL), were added 3-tert-butylaniline (152 mg, 1.02 mmol), DMAP (125 mg, 1.02 mmol) and then EDCI (196 mg, 1.02 mmol). The reaction was stirred for 18 h., and then diluted with DCM and washed with water and brine. The organic solution was dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to yield the title compound as a white solid (389 mg, 86%). LCMS: (FA) ES+ 490.2 (M+1), ES− 488.2 (M−1).

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic solution was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-bef0a679ce664f32a056442afbf3e91a
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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