Potassium Carbonate → HCID 11433230, compound

HRID 2421021Notes

Reaction equation

HRID 2421021 reaction equation
Cl[C:2]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[C:5]([C:6]([NH:8][CH2:9][C@@H:10]([OH:27])[CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([O:18][C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=3)[CH2:14][CH2:13]2)=[O:7])=[CH:4][N:3]=1.[CH3:34][S:35]([NH2:38])(=[O:37])=[O:36].C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O>[Cl:26][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][C:22]=1[Cl:25])[O:18][CH:15]1[CH2:16][CH2:17][N:12]([CH2:11][C@H:10]([OH:27])[CH2:9][NH:8][C:6](=[O:7])[C:5]2[C:28]([C:30]([F:32])([F:31])[F:33])=[CH:29][C:2]([NH:38][S:35]([CH3:34])(=[O:37])=[O:36])=[N:3][CH:4]=2)[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 72879MethanesulfonamideHCID 86611245HCID 86611245, compound

Product 1

HCID 11433230HCID 11433230, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A stirred solution of 6-chloro-N-{(2R)-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-2-hydroxypropyl}-4-(trifluoromethyl)nicotinamide (0.28 g), methanesulfonamide (0.12 g) and potassium carbonate (0.148 g) in N-methyl-2-pyrrolidinone was heated under microwave irradiation (100 W) at 100° C. for 15 min. The reaction mixture was concentrated in vacuo and redissolved in 4:1:1 acetonitrile/water/acetic acid (6 mL) and subjected to RPHPLC (gradient 0.1% ammonium acetate/acetonitrile 95% to 5%) to yield a white solid (0.025 g).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionredissolved in 4:1:1 acetonitrile/water/acetic acid (6 mL)

Sources & evidence

ORD record
ord-992c473dd842494da37580357080660b
Source dataset
uspto-grants-2011_06
Patent number
US07956070B2

Reaction notes

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