Reaction equation
[CH3:1][N:2]([CH2:4][C:5](Cl)=[O:6])[CH3:3].[N:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[C:15]([C:22]2[C:31]3[C:26](=[CH:27][C:28]([NH2:32])=[CH:29][CH:30]=3)[N:25]=[CH:24][CH:23]=2)=[C:16]2[CH2:21][CH2:20][CH2:19][N:17]2[N:18]=1.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[CH3:1][N:2]([CH3:3])[CH2:4][C:5]([NH:32][C:28]1[CH:27]=[C:26]2[C:31]([C:22]([C:15]3[C:14]([C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][N:8]=4)=[N:18][N:17]4[CH2:19][CH2:20][CH2:21][C:16]=34)=[CH:23][CH:24]=[N:25]2)=[CH:30][CH:29]=1)=[O:6]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of dimethylamino-acetyl chloride (620.0 mg, 13.33 mmol), 4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-ylamine (75 mg, 0.23 mmol), and 4-N,N-dimethylaminopyridine (10.2 mg, 0.09 mmol) in dry pyridine (1 mL) is refluxed for 72 h. The mixture is treated with saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic layer is washed with brine, dried (sodium sulfate), concentrated in vacuo, and the residue chromatographed on SiO2 ((5% to 20% methanol in dichloromethane) to yield a yellow oil, 62.3 mg (67%).
Workup
- temperatureis refluxed for 72 h
- extractionextracted with ethyl acetate
- washThe organic layer is washed with brine
- dry with materialdried (sodium sulfate)
- concentrationconcentrated in vacuo
- customthe residue chromatographed on SiO2 ((5% to 20% methanol in dichloromethane)
- customto yield a yellow oil, 62.3 mg (67%)
Sources & evidence
- ORD record
- ord-e9568a52249c4b2fbdc93d52e5bffe68
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07087626B2
Linked notes
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