3-Amino-4-methylbenzoic acid → HCID 68288889, compound

HRID 541239Notes

Reaction equation

HRID 541239 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH:14]3[CH:10]2[CH2:11][NH:12][CH2:13]3)=[CH:5][CH:4]=1.[NH2:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=1[CH3:25])[C:19](O)=[O:20].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[NH2:15][C:16]1[CH:17]=[C:18]([C:19]([N:12]2[CH2:13][CH:14]3[CH:10]([CH:9]3[C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH2:11]2)=[O:20])[CH:22]=[CH:23][C:24]=1[CH3:25]

Participants

8

Reactant 6

HCID 755683-Amino-4-methylbenzoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68288882HCID 68288882, compound

Product 1

HCID 68288889HCID 68288889, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-(4-Methoxyphenyl)-3-azabicyclo[3.1.0]hexane (0.124 g, 0.82 mmol), 3-amino-4-methylbenzoic acid (0.155 g, 0.82 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI, 0.172 g, 0.90 mmol), 1-hydroxybenzotriazole (˜20% H2O, 0.122 g, 0.90 mmol) and diisopropylethylamine (0.71 mL, 4.1 mmol) in DMF (3 mL) was stirred at room temperature overnight. The reaction mixture was poured into saturated aqueous NaHCO3 and extracted with EtOAc (3×). The combined organic extract was dried over MgSO4, filtered and concentrated. The residue was purified by flash column chromatography with EtOAc in hexane (60%, then 100%) to give the title compound as a white foam (0.15 g, 57% yield).

Workup

  1. extractionextracted with EtOAc (3×)
  2. extractionThe combined organic extract
  3. dry with materialwas dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography with EtOAc in hexane (60%

Sources & evidence

ORD record
ord-11e59480eb2b45f59008c56f1279ab2d
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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