1-Hydroxybenzotriazole → HCID 57970077, compound

HRID 1666620Notes

Reaction equation

HRID 1666620 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([NH:13][C@H:14]1[CH2:18][CH2:17][NH:16][CH2:15]1)[CH:7]=[C:6]2[CH3:19].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2([C:31](O)=[O:32])[CH2:30][CH2:29][CH2:28]2)=[CH:23][CH:22]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.C(=O)([O-])O.[Na+]>C(OCC)(=O)C.O.CN(C=O)C>[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]2([C:31]([N:16]3[CH2:17][CH2:18][C@H:14]([NH:13][C:8]4[CH:7]=[C:6]([CH3:19])[C:5]5[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=5)[N:9]=4)[CH2:15]3)=[O:32])[CH2:30][CH2:29][CH2:28]2)=[CH:25][CH:26]=1

Participants

9

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 6027611-(p-Chlorophenyl)cyclobutanecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57970090HCID 57970090, compound

Product 1

HCID 57970077HCID 57970077, compoundYield 76.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of (S)-6-methoxy-4-methyl-N-(pyrrolidin-3-yl)quinolin-2-amine (0.50 g), 1-(4-chlorophenyl)-1-cyclobutane carboxylic acid (0.41 g), and DMF (6 mL) were added HOBt (0.39 g) and EDC.HCl (0.56 g), and the mixture was stirred at room temperature for 12 h. The reaction mixture was diluted with ethyl acetate and water, followed by addition of a saturated sodium hydrogencarbonate solution to extract the mixture. The organic layer was dried with anhydrous magnesium sulfate, then the desiccant was removed by filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (silica gel, chloroform/methanol, and NH silica gel, ethyl acetate) to obtain colorless amorphous (S)-(1-(4-chlorophenyl)cyclobutyl)-(3-(6-methoxy-4-methylquinolin-2-ylamino)pyrrolidin-1-yl)methanone (0.67 g).

Workup

  1. extractionto extract the mixture
  2. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  3. customthe desiccant was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (silica gel, chloroform/methanol, and NH silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-3d31d53a979148eda1563c2d7693ef9d
Source dataset
uspto-grants-2011_10
Patent number
US08044068B2

Reaction notes

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