1-Methylpiperazine → 8-bromo-1-{3-methyl-1-[2-(4-methyl-piperazin-1-yl)-2-oxo-ethyl]-1H-pyrazol-4-yl}-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

HRID 445690Notes

Reaction equation

HRID 445690 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[NH:12][C:13](=[O:25])[N:14]([C:15]4[C:16]([CH3:24])=[N:17][N:18]([CH2:20][C:21]([OH:23])=O)[CH:19]=4)[C:5]=3[C:4]=2[CH:3]=1.[B-](F)(F)(F)F.CN(C(ON1C(=O)C=CC=C1)=[N+](C)C)C.[CH3:46][N:47]1[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1>CC(N(C)C)=O>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[NH:12][C:13](=[O:25])[N:14]([C:15]4[C:16]([CH3:24])=[N:17][N:18]([CH2:20][C:21]([N:50]5[CH2:51][CH2:52][N:47]([CH3:46])[CH2:48][CH2:49]5)=[O:23])[CH:19]=4)[C:5]=3[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 531671-Methylpiperazine2×HCID 2733204O-(2-Oxo-1(2H)-pyridyl)-N,N,N',N'-tetramethyluronium TetrafluoroborateHCID 59619756[4-(8-Bromo-2-oxo-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl)-3-methyl-pyrazol-1-yl]-acetic acid

Product 1

HCID 596198958-bromo-1-{3-methyl-1-[2-(4-methyl-piperazin-1-yl)-2-oxo-ethyl]-1H-pyrazol-4-yl}-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of [4-(8-bromo-2-oxo-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl)-3-methyl-pyrazol-1-yl]-acetic acid (Stage 101.1.2, 178 mg, 0.443 mmol), DIPE (0.232 ml, 1.33 mmol), TPTU (223 mg, 0.752 mmol) in DMA (5 ml) was stirred at rt for 5 min, then was added N-methylpiperazine (0.1 ml, 0.90 mmol). The reaction mixture was stirred 19 h at rt and then was added N-methylpiperazine (0.1 ml, 0.90 mmol) and the reaction mixture was stirred 25 h at rt. The reaction mixture was purified by prep. HPLC to give the title compound as an off-white solid. (HPLC: tR 1.98 min (Method A); M+H=484, 486 MS-ES)

Workup

  1. stirringthe reaction mixture was stirred 25 h at rt
  2. customThe reaction mixture was purified by prep

Sources & evidence

ORD record
ord-5b1ce173aa6d44cd896f8bd6c1f31b9f
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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