Potassium Hydroxide → HCID 67350841, compound

HRID 1029045Notes

Reaction equation

HRID 1029045 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.[C@H:24]12[CH2:33][C@H:27]([N:28]([CH2:30][C:31]#[N:32])[CH2:29]1)[CH2:26][O:25]2.[OH-].[K+]>CS(C)=O>[NH2:32][C:31]1[C:30]([N:28]2[CH2:29][C@@H:24]3[CH2:33][C@H:27]2[CH2:26][O:25]3)=[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[CH2:17][CH2:18][CH2:19][CH2:20]3)=[O:15])[CH:4]=2)[N:1]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 86676845HCID 86676845, compoundHCID 86676846HCID 86676846, compound

Product 1

HCID 67350841HCID 67350841, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of 4-amino-2′-methyl-6′-(pyrrolidine-1-carbonyl)biphenyl-3-carbaldehyde (0.100 g, 0.324 mmol) in DMSO (3.0 mL) was added to an 80° C. solution of 2-((1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)acetonitrile (0.067 g, 0.486 mmol) and potassium hydroxide (0.016 g, 0.28 mmol) (11 M aq., 44 uL) in DMSO (1.25 mL) in 4 portions at 15 min intervals. The resulting mixture was heated for 18 h, cooled, filtered and purified by prep HPLC (12-51% CH3CN/water, 0.1% TFA) to give (2-(2-amino-3-((1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)quinolin-6-yl)-3-methylphenyl)(pyrrolidin-1-yl)methanone as a yellow solid. MS (ESI, pos. ion) m/z: 429 (M+1).

Workup

  1. temperatureThe resulting mixture was heated for 18 h
  2. temperaturecooled
  3. filtrationfiltered
  4. custompurified by prep HPLC (12-51% CH3CN/water, 0.1% TFA)

Sources & evidence

ORD record
ord-31006ae74c1c435dac45ae58dcd3ca96
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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