Methyl 2-[4-(aminomethyl)phenyl]benzoate → HCID 11347923, compound

HRID 1711495Notes

Reaction equation

HRID 1711495 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:4]=1.[OH:19][C:20]1([C:23](O)=[O:24])[CH2:22][CH2:21]1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>C1COCC1.C(Cl)Cl.C(Cl)Cl>[OH:19][C:20]1([C:23]([NH:1][CH2:2][C:3]2[CH:8]=[CH:7][C:6]([C:9]3[C:10]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:12]=[CH:13][CH:14]=3)=[CH:5][CH:4]=2)=[O:24])[CH2:22][CH2:21]1

Participants

7

Reactant 4

HCID 1393434Methyl 2-[4-(aminomethyl)phenyl]benzoateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27331601-Hydroxy-1-cyclopropanecarboxylic acidHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 11347923HCID 11347923, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

Methyl 4′-(aminomethyl)biphenyl-2-carboxylate (0.325 g, 1.35 mmol), 1-hydroxycyclo-propanecarboxylic acid (0.151 g, 1.48 mmol) and 1-hydroxybenzotriazole hydrate (0.248 g, 1.62 mmol) were suspended in a mixture of THF/DCM (13 mL of THF/6.5 mL of DCM), followed by the addition of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.336 g, 1.75 mmol). Rapidly the solution turned homogenous, but returned to a heterogeneous mixture after 5 minutes. After 3 hours the solvent mixture was exchanged for pure DCM, prior to purification by silica gel chromatography eluted with 1-5% methanol in DCM to provide the title compound.

Workup

  1. customto purification by silica gel chromatography
  2. washeluted with 1-5% methanol in DCM

Sources & evidence

ORD record
ord-323d783c164f4110a53deb704077611d
Source dataset
uspto-grants-2010_09
Patent number
US07790754B2

Reaction notes

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