1-Methylpiperazine → HCID 59832200, compound

HRID 269515Notes

Reaction equation

HRID 269515 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([CH:21]3[CH2:23][CH:22]3[C:24]([OH:26])=O)[CH:19]=2)[NH:14][CH:13]=1)=[O:11].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:60][N:61]1[CH2:66][CH2:65][NH:64][CH2:63][CH2:62]1>CN(C=O)C>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([C@@H:21]3[CH2:23][C@H:22]3[C:24]([N:64]3[CH2:65][CH2:66][N:61]([CH3:60])[CH2:62][CH2:63]3)=[O:26])[CH:19]=2)[NH:14][CH:13]=1)=[O:11]

Participants

6

Reactant 4

HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59832323HCID 59832323, compound

Product 1

HCID 59832200HCID 59832200, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-{3-[(2,3-Difluoro-phenyl)-acetyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-cyclopropanecarboxylic acid, (93 mg, 0.26 mmol), was combined with DIEA, (67 mg, 0.52 mmol), and HBTU, (113 mg, 0.3 mmol) in 1 mL DMF and stirred at rt for ˜15 min. Then N-methyl piperazine, (26 mg, 0.26 mmol), was added and the reaction stirred at rt for 4 hours. The DMF was evaporated under vacuum, water added and the suspension extracted with dichloromethane. The solvent was evaporated under vacuum and the residue purified by silica chromatography, (eluent: 5% methanol/DCM), affording trans-2-(2,3-Difluoro-phenyl)-1-{5-[2-(4-methyl-piperaz ine-1-carbonyl)-cyclopropyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-ethanone, (35 mg, Rf 0.5) and the cis isomer (16 mg, Rf 0.3).

Workup

  1. stirringthe reaction stirred at rt for 4 hours
  2. customThe DMF was evaporated under vacuum, water
  3. additionadded
  4. extractionthe suspension extracted with dichloromethane
  5. customThe solvent was evaporated under vacuum
  6. customthe residue purified by silica chromatography, (eluent: 5% methanol/DCM),

Sources & evidence

ORD record
ord-6040e632d19b42a2a26bc3ce59f48caf
Source dataset
uspto-grants-2008_11
Patent number
US07446199B2

Reaction notes

Loading…