Acetone → HCID 178482190, compound

HRID 1639993Notes

Reaction equation

HRID 1639993 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:25][CH2:24][CH2:23][C@@:10]2([C:14](=[O:15])[N:13]([C@H:16]3[CH2:21][CH2:20][C@H:19]([OH:22])[CH2:18][CH2:17]3)[CH2:12][CH2:11]2)[CH2:9]1.CI.[C:33](=O)([O-])[O-].[K+].[K+].CC(C)=O>>[F:1][C:2]1[CH:3]=[C:4]([N:26]([CH3:33])[S:27]([CH3:30])(=[O:29])=[O:28])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:25][CH2:24][CH2:23][C@@:10]2([C:14](=[O:15])[N:13]([C@H:16]3[CH2:17][CH2:18][C@H:19]([OH:22])[CH2:20][CH2:21]3)[CH2:12][CH2:11]2)[CH2:9]1

Participants

5

Reactant 4

HCID 180AcetoneHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178505029HCID 178505029, compound

Product 1

HCID 178482190HCID 178482190, compound

Procedure

A mixture of N-{3-fluoro-4-[(5S)-2-(trans-4-hydroxycyclohexyl)-1-oxo-2,7-diazaspiro[4.5]dec-7-yl]phenyl}methanesulfonamide (20 mg, 0.00006 mol, example 312), methyl iodide (4.1 μL, 0.000066 mol), and potassium carbonate (10 mg, in excess) in acetone (2 mL, 0.03 mol) was stirred at rt for 2 h and then heated to 40° C. for 2 h. The reaction mixture was allowed to cool to rt and was purified by prep-HPLC to afford the desired product. LC-MS: 454.2 (M+H)+.

Workup

  1. temperatureheated to 40° C. for 2 h
  2. temperatureto cool to rt
  3. customwas purified by prep-HPLC

Sources & evidence

ORD record
ord-e2eca789b45a474db8c5c53b0107f3de
Source dataset
uspto-grants-2012_02
Patent number
US08110581B2

Reaction notes

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