Diisopropylethylamine → (R)-(6-Methoxy-pyridin-2-yl)-[2-methyl-4-(1-m-tolyl-1H-[1,2,4]-triazole-3-carbonyl)-piperazin-1-yl]-methanone

HRID 334091Notes

Reaction equation

HRID 334091 reaction equation
[CH3:1][C@H:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]([C:10]2[N:14]=[CH:13][N:12]([C:15]3[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=3)[N:11]=2)=[O:9])[CH2:3]1.[CH3:22][O:23][C:24]1[N:29]=[C:28]([C:30](O)=[O:31])[CH:27]=[CH:26][CH:25]=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>[CH3:22][O:23][C:24]1[N:29]=[C:28]([C:30]([N:7]2[CH2:6][CH2:5][N:4]([C:8]([C:10]3[N:14]=[CH:13][N:12]([C:15]4[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=4)[N:11]=3)=[O:9])[CH2:3][C@H:2]2[CH3:1])=[O:31])[CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5708916-Methoxypicolinic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86688312((R)-3-methyl-piperazin-1-yl)-(1-m-tolyl-1H-[1,2,4]-triazol-3-yl)-methanone

Product 1

HCID 86688311(R)-(6-Methoxy-pyridin-2-yl)-[2-methyl-4-(1-m-tolyl-1H-[1,2,4]-triazole-3-carbonyl)-piperazin-1-yl]-methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 86 mg (0.30 mmol) ((R)-3-methyl-piperazin-1-yl)-(1-m-tolyl-1H-[1,2,4]-triazol-3-yl)-methanone, 46 mg (0.30 mmol) 6-methoxy-pyridine-2-carboxylic acid, 0.11 g (0.33 mmol) TBTU and 80 μL (0.45 mmol) DIPEA in 5.0 mL DMF was stirred at RT for 12 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-beee48e611c1440e9a21c083164eafeb
Source dataset
uspto-grants-2014_11
Patent number
US08883789B2

Reaction notes

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