1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58503979, compound

HRID 2407665Notes

Reaction equation

HRID 2407665 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[O:11][CH3:12].C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[C:44]1([C:50]2[CH:54]=[C:53]([CH2:55][N:56]3[CH2:61][CH2:60][CH:59]([CH2:62][NH2:63])[CH2:58][CH2:57]3)[O:52][N:51]=2)[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:63][CH2:62][CH:59]2[CH2:58][CH2:57][N:56]([CH2:55][C:53]3[O:52][N:51]=[C:50]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[CH:54]=3)[CH2:61][CH2:60]2)=[O:8])=[CH:4][C:3]=1[O:11][CH3:12]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 20633784-Chloro-3-methoxybenzoic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 58504252HCID 58504252, compound

Product 1

HCID 58503979HCID 58503979, compoundYield 45.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-chloro-3-methoxybenzoic acid (65 mg) in dichloromethane (4 mL) was added 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide (67 mg), 1-hydroxybenzotriazole hydrate (58 mg), and diisopropylethylamine (0.25 mL). The mixture was stirred at room temperature for five minutes and then the hydrochloride salt of the compound prepared in Example 9 (100 mg) was added. The reaction mixture was stirred at room temperature for 16 hours. The organic phase was diluted with ethyl acetate, washed with a saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:1, then ethyl acetate) to obtain the title compound (70 mg) having the following physical data.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 16 hours
  2. washwashed with a saturated aqueous sodium bicarbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate

Sources & evidence

ORD record
ord-544ac211be2a427eb8bbd397009d4a50
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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