Potassium Carbonate → HCID 53390500, compound

HRID 400394Notes

Reaction equation

HRID 400394 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([S:8]([C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=2[O:19][C:20]2[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=2)[C:14]#[N:15])(=[O:10])=[O:9])[CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[Cl:34][CH2:35][CH2:36][N:37]=[C:38]=[O:39]>C1COCC1>[NH2:1][CH:2]1[CH2:3][CH2:4][N:5]([S:8]([C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=2[O:19][C:20]2[CH:21]=[C:22]([Cl:27])[CH:23]=[C:24]([Cl:26])[CH:25]=2)[C:14]#[N:15])(=[O:10])=[O:9])[CH2:6][CH2:7]1.[Cl:34][CH2:35][CH2:36][NH:37][C:38]([NH:1][CH:2]1[CH2:3][CH2:4][N:5]([S:8]([C:11]2[CH:12]=[C:13]([C:14]#[N:15])[CH:16]=[CH:17][C:18]=2[O:19][C:20]2[CH:21]=[C:22]([Cl:27])[CH:23]=[C:24]([Cl:26])[CH:25]=2)(=[O:10])=[O:9])[CH2:6][CH2:7]1)=[O:39]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 160352-Chloroethyl isocyanateHCID 58442575HCID 58442575, compound

Product 2

HCID 53390500HCID 53390500, compoundHCID 58442575HCID 58442575, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(4-aminopiperidin-1-ylsulfonyl)-4-(3,5-dichlorophenoxy)benzonitrile was prepared following the procedure of Example 1. The final product was prepared by dissolving 3-(4-aminopiperidin-1-ylsulfonyl)-4-(3,5-dichlorophenoxy)benzonitrile (1.00 g) in THF (30 mL) followed by the addition potassium carbonate (975 mg, 3.0 eq.), then 2-chloroethyl isocyanate (496 mg, 2.0 eq.) dropwise. After stirring for 1 hour, the starting material was consumed (confirmed by HPLC), and the mixture was filtered to remove potassium carbonate. The resulting filtrate was concentrated in vacuo, the solid triturated with dichlormethane and isopropyl ether, and fitted to obtain a white powder (838 mg, 67% yield, 97% purity).

Workup

  1. customthe starting material was consumed (confirmed by HPLC)
  2. filtrationthe mixture was filtered
  3. customto remove potassium carbonate
  4. concentrationThe resulting filtrate was concentrated in vacuo
  5. customthe solid triturated with dichlormethane and isopropyl ether
  6. customfitted
  7. customto obtain a white powder (838 mg, 67% yield, 97% purity)

Sources & evidence

ORD record
ord-c6d30092b8294ae2804d2217d2f385d5
Source dataset
uspto-grants-2014_06
Patent number
US08741894B2

Reaction notes

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