4-Methoxybenzylamine → HCID 57752777, compound

HRID 1888542Notes

Reaction equation

HRID 1888542 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([B:10]([OH:12])[OH:11])[CH:7]=[CH:8][CH:9]=1)([OH:3])=O.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH3:65][O:66][C:67]1[CH:72]=[CH:71][C:70]([CH2:73][NH2:74])=[CH:69][CH:68]=1>CN(C=O)C>[CH3:65][O:66][C:67]1[CH:72]=[CH:71][C:70]([CH2:73][NH:74][C:1]([C:4]2[CH:5]=[C:6]([B:10]([OH:12])[OH:11])[CH:7]=[CH:8][CH:9]=2)=[O:3])=[CH:69][CH:68]=1

Participants

7

Reactant 5

HCID 754524-MethoxybenzylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 27339573-Carboxyphenylboronic acid

Product 1

HCID 57752777HCID 57752777, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Carboxyphenylboronic acid (140 mg, 0.84 mmol), PyBOP (376 mg, 0.72 mmol) and HOBt (97.7 mg, 0.72 mmol) were dissolved in DMF (3.18 mL) and treated with DIPEA (420 μL, 2.41 mmol). After 5 min at ambient temperature, 4-methoxybenzenemethanamine (78 μL, 0.60 mmol) was added. The homogeneous reaction mixture was stirred at ambient temperature for 16 h, the solvent was removed under reduced pressure, and the residue purified by preparative HPLC (5-40% MeCN over 40 min, 35 mL/min) to afford the product as a white solid.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customthe residue purified by preparative HPLC (5-40% MeCN over 40 min, 35 mL/min)

Sources & evidence

ORD record
ord-f48252e695f7481483b4c1767ccd1299
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

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