Ethyl 3-aminobenzoate → HCID 18185342, compound

HRID 1358781Notes

Reaction equation

HRID 1358781 reaction equation
C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[CH3:34][N:35]([CH2:43][C:44]1[CH:45]=[C:46]2[C:51](=[CH:52][CH:53]=1)[CH:50]=[C:49]([C:54]([OH:56])=O)[CH:48]=[CH:47]2)[S:36]([C:39]([F:42])([F:41])[F:40])(=[O:38])=[O:37].C([O:59][C:60](=[O:68])[C:61]1[CH:66]=[CH:65][CH:64]=[C:63]([NH2:67])[CH:62]=1)C.[OH-].[Na+]>C(Cl)Cl.CN(C1C=CN=CC=1)C.CO.O>[CH3:34][N:35]([CH2:43][C:44]1[CH:45]=[C:46]2[C:51](=[CH:52][CH:53]=1)[CH:50]=[C:49]([C:54]([NH:67][C:63]1[CH:62]=[C:61]([CH:66]=[CH:65][CH:64]=1)[C:60]([OH:68])=[O:59])=[O:56])[CH:48]=[CH:47]2)[S:36]([C:39]([F:41])([F:40])[F:42])(=[O:38])=[O:37]

Participants

9

Reactant 4

HCID 11400Ethyl 3-aminobenzoateHCID 14798Sodium Hydroxide2×HCID 2724699PyBOPHCID 18185300HCID 18185300, compound

Product 1

HCID 18185342HCID 18185342, compoundYield 37%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

PyBOP (604 mg, 1.16 mmol) was added to the mixture of 6-[(Methyl-trifluoromethanesulfonyl-amino-)-methyl]-naphthalene-2-carboxylic acid (200 mg, 0.58 mmol), ethyl-3-amino-benzoate (86 ul, 0.58 mmol) in DCM (5 ml), followed by addition of DMAP (106 mg, 0.87 mmol). Allowed the mixture stirred at room temperature for overnight. Added more DCM, washed with 1N HCl, NaHCO3(sat.), and brine. Evaporated the solvent to give a white solid which was dissolved in 10 ml of methanol, added NaOH (5 eq, 116 mg) in H2O (10 ml), stirred at room temperature for overnight. Added more H2O and NaOH, then washed with DCM. Separated the DCM, the aqueous layer was acidified with 6N HCl, the resulting white solid was collected by vacuum filtration, washed with H2O, vacuum dry to get 100 mg of 3-({6-[(Methyl-trifluoromethanesulfonyl-amino)-methyl]-naphthalene-2-carbonyl}-amino)-benzoic acid.

Workup

  1. washwashed with 1N HCl, NaHCO3(sat.), and brine
  2. customEvaporated the solvent
  3. customto give a white solid which
  4. stirringstirred at room temperature for overnight
  5. washwashed with DCM
  6. customSeparated the DCM
  7. filtrationthe resulting white solid was collected by vacuum filtration
  8. washwashed with H2O, vacuum
  9. customdry

Sources & evidence

ORD record
ord-bd370b88e3b24829a7f6911e41cc1dd9
Source dataset
uspto-grants-2003_07
Patent number
US06596772B1

Reaction notes

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