Diisopropylethylamine → (4-Benzyl-3-methoxymethyl-3-methyl-piperazin-1-yl)-(6-methoxy-pyridin-2-yl)-methanone

HRID 334084Notes

Reaction equation

HRID 334084 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=1.[CH2:12]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][C:20]1([CH2:26][O:27][CH3:28])[CH3:25])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:12]([N:19]1[CH2:24][CH2:23][N:22]([C:9]([C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[N:8]=2)=[O:11])[CH2:21][C:20]1([CH2:26][O:27][CH3:28])[CH3:25])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5708916-Methoxypicolinic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 866883061-Benzyl-2-methoxymethyl-2-methyl-piperazine

Product 1

HCID 86688307(4-Benzyl-3-methoxymethyl-3-methyl-piperazin-1-yl)-(6-methoxy-pyridin-2-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 77.6 mg (507 μmol) 6-methoxy-2-pyridinecarboxylic acid, 125 mg (507 μmol) 1-benzyl-2-methoxymethyl-2-methyl-piperazine, 177 mg (551 μmol) TBTU and 100 μL (581 μmol) DIPEA in 1.5 mL DMF was stirred at RT for 2 h. The reaction mixture was poured into ice water and extracted with EtOAc. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f017a9b597cc457a90f9fe290f9a6e1b
Source dataset
uspto-grants-2014_11
Patent number
US08883789B2

Reaction notes

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