Triethylamine → HCID 58804653, compound

HRID 349246Notes

Reaction equation

HRID 349246 reaction equation
ClC1C(Cl)=CC(N[C:13](=O)[CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:18][CH:17]=2)=CC=1C(O)=O.[NH2:35][C:36]1[CH:37]=[C:38]([CH:43]=[CH:44][C:45]=1[NH2:46])[C:39]([O:41][CH3:42])=[O:40].C(N(CC)CC)C>ClCCl>[C:28]1([CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][O:22][C:19]2[CH:20]=[CH:21][C:16]([CH2:15][CH2:14][C:13]3[NH:35][C:36]4[CH:37]=[C:38]([C:39]([O:41][CH3:42])=[O:40])[CH:43]=[CH:44][C:45]=4[N:46]=3)=[CH:17][CH:18]=2)[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1355243,5-Diamino-2-methylbenzoic acidHCID 10163948HCID 10163948, compound

Product 1

HCID 58804653HCID 58804653, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound prepared in Reference Example 3 which prepared by the same procedure as described in Example 3 using the compound prepared in Reference Example 2 (150 mg) in dichloromethane (5 mL) was added methyl 3,4-diaminobenzoate (160 mg) and triethylamine (0.34 mL). The reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated. To a solution of the obtained residue in toluene (10 mL) was added p-toluenesulfonate (50 mg). The reaction mixture was refluxed overnight. Saturated aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, which was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous sodium sulfate and concentrated. The obtained residue was washed with diisopropyl ether to give the compound of the present invention (99 mg) having the following physical data.

Workup

  1. customTo a solution of the compound prepared in Reference Example 3 which
  2. customprepared by the same procedure
  3. concentrationThe reaction mixture was concentrated
  4. additionTo a solution of the obtained residue in toluene (10 mL) was added p-toluenesulfonate (50 mg)
  5. temperatureThe reaction mixture was refluxed overnight
  6. additionSaturated aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, which
  7. extractionwas extracted with ethyl acetate
  8. washThe extract was washed with brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated
  11. washThe obtained residue was washed with diisopropyl ether
  12. customto give the compound of the present invention (99 mg)

Sources & evidence

ORD record
ord-593cdc7081ce47a680d70be8f366ebe8
Source dataset
uspto-grants-2007_02
Patent number
US07179817B2

Reaction notes

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