Potassium Hydroxide → HCID 53330058, compound

HRID 1029046Notes

Reaction equation

HRID 1029046 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])=[CH:12][CH:11]=[CH:10][C:9]=2[CH3:21])=[CH:4][C:3]=1[CH:22]=O.[OH-].[K+].[C:26]1([CH2:31][C:32]#[N:33])[CH2:30][CH2:29][CH2:28][CH:27]=1>CS(C)=O>[NH2:33][C:32]1[C:31]([C:26]2[CH2:30][CH2:29][CH2:28][CH:27]=2)=[CH:22][C:3]2[C:2](=[CH:7][CH:6]=[C:5]([C:8]3[C:9]([CH3:21])=[CH:10][CH:11]=[CH:12][C:13]=3[C:14]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])[CH:4]=2)[N:1]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 89811Cyclopent-1-ene-1-acetonitrileHCID 86676845HCID 86676845, compound

Product 1

HCID 53330058HCID 53330058, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 4-amino-2′-methyl-6′-(pyrrolidine-1-carbonyl)biphenyl-3-carbaldehyde (0.040 g, 0.13 mmol, prepared as in Example 57, Steps 2-5), KOH (10.9 mg, 0.195 mmol) (11 M solution, 18 uL), 1-cyclopenteneacetonitrile (0.022 mL, 0.20 mmol) and DMSO (0.8 mL) was heated in a Biotage microwave at 140° C. for 5 min. LCMS indicated good conversion to desired product. The crude material was purified by prep HPLC (21-60% CH3CN/water modified with 0.1% TFA), and again by prep HPLC (10-90% CH3CN/water modified with 0.1% NH4OH) to give (2-(2-amino-3-cyclopentenylquinolin-6-yl)-3-methylphenyl)(pyrrolidin-1-yl)methanone as a yellow solid. MS (ESI, pos. ion) m/z: 398 (M+1).

Sources & evidence

ORD record
ord-caee96b0ddad46a8a162a35451ac8c64
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

Loading…