Propyl isocyanate → HCID 59759894, compound

HRID 416519Notes

Reaction equation

HRID 416519 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([NH:10][S:11]([CH2:14][CH2:15][NH:16][C:17]([C:19]2[S:20][C:21]([Cl:24])=[CH:22][CH:23]=2)=[O:18])(=[O:13])=[O:12])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[N:25]([CH2:28][CH2:29][CH3:30])=[C:26]=[O:27]>ClCCl.CN(C1C=CN=CC=1)C>[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([N:10]([C:26]([NH:25][CH2:28][CH2:29][CH3:30])=[O:27])[S:11]([CH2:14][CH2:15][NH:16][C:17]([C:19]2[S:20][C:21]([Cl:24])=[CH:22][CH:23]=2)=[O:18])(=[O:12])=[O:13])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 61033Propyl isocyanate2×HCID 119904785-Chloro-Thiophene-2-Carboxylic Acid [2-(1--Isopropyl-Piperidin-4-Ylsulfamoyl)-Ethyl]-Amide

Product 1

HCID 59759894HCID 59759894, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of 200 mg (0.50 mmol) 5-chloro-thiophene-2-carboxylic acid [2-(1-isopropyl-piperidin-4-ylsulfamoyl)-ethyl]-amide in 3 ml dichloromethane were added 0.1 ml (2 equiv.) 1-isocyanato-propane and 6 mg DMAP. The reaction mixture was stirred overnight at room temperature. The next day further 0.1 ml (2 equiv.) 1-isocyanato-propane and 6 mg DMAP were added. After stirring for 48 h at room temperature, the reaction mixture was washed with 3 ml water and concentrated under reduced pressure. Final purification by preparative RP-HPLC (CH3CN/H2O gradient+0.1% TFA) gave pure 5-chloro-thiophene-2-carboxylic acid {2-[(1-isopropyl-piperidin-4-yl)-propylaminocarbonyl-sulfamoyl]-ethyl}-amide. The title compound was obtained as its trifluoroacetate in form of a colorless amorphous material.

Workup

  1. stirringAfter stirring for 48 h at room temperature
  2. washthe reaction mixture was washed with 3 ml water
  3. concentrationconcentrated under reduced pressure
  4. customFinal purification by preparative RP-HPLC (CH3CN/H2O gradient+0.1% TFA)

Sources & evidence

ORD record
ord-89aa969c664548b48ef08c5d5201a76d
Source dataset
uspto-grants-2012_01
Patent number
US08088925B2

Reaction notes

Loading…