Potassium Carbonate → HCID 57986836, compound

HRID 1408353Notes

Reaction equation

HRID 1408353 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[S:16][C:17]([CH2:20]Cl)=[CH:18][N:19]=2)([F:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:22][S:23]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)(=[O:25])=[O:24].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([F:14])([C:15]2[S:16][C:17]([CH2:20][O:32][C:29]3[CH:28]=[CH:27][C:26]([S:23]([CH3:22])(=[O:25])=[O:24])=[CH:31][CH:30]=3)=[CH:18][N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1233504-(Methylsulfonyl)phenolHCID 57986899HCID 57986899, compound

Product 1

HCID 57986836HCID 57986836, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-(5-Chloromethyl-thiazol-2-yl)-4-fluoro-piperidine-1-carboxylic acid tert-butyl ester (1.42 g, 4.24 mmol), 4-methanesulfonyl-phenol (731 mg, 1.0 eq.) and K2CO3 (878 mg, 1.5 eq.) in acetone (30 mL) was heated to reflux overnight. After cooling, the solid was filtered off through a pad of celite. The filtrate was concentrated in vacuo. The crude product was purified on silica gel (EtOAc:hexanes=1:1) to afford the desired product as a white solid. 1H NMR (CDCl3): δ 7.86 (2H, d, J=9.2 Hz), 7.35 (1H, s), 7.10 (2H, d, J=9.2 Hz), 5.22 (2H, s), 4.08 (2H, br), 3.19 (2H, br), 3.02 (3H, s), 2.05˜2.32 (4H, m), 1.46 (9H, s).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. temperatureAfter cooling
  4. filtrationthe solid was filtered off through a pad of celite
  5. concentrationThe filtrate was concentrated in vacuo
  6. customThe crude product was purified on silica gel (EtOAc:hexanes=1:1)

Sources & evidence

ORD record
ord-d04fb68a285443fe91d086f2d82a6866
Source dataset
uspto-grants-2014_12
Patent number
US08921350B2

Reaction notes

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