2-Bromopropane → HCID 66624418, compound

HRID 416501Notes

Reaction equation

HRID 416501 reaction equation
Br[CH:2]([CH3:4])[CH3:3].Cl.[NH:6]1[CH2:9][CH:8]([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])[CH2:7]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.ClCCl>[CH:2]([N:6]1[CH2:9][CH:8]([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:12])=[O:13])[CH2:7]1)([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 66625235HCID 66625235, compound

Product 1

HCID 66624418HCID 66624418, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

85.3 mg (5 equiv.) 2-Bromo-propane were added to a mixture of 50 mg (0.14 mmol) 5-chloro-thiophene-2-carboxylic acid[2-(azetidin-3-ylsulfamoyl)-ethyl]-amide hydrochloride and 38 mg (2 equiv.) K2CO3 in 5 ml DMF. The resulting mixture was stirred for 2 h at 70° C., then diluted with 15 ml dichloromethane and washed with 3 ml of a saturated NaHCO3-solution. The organic phase was dried over anhydrous MgSO4 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-azetidin-3-ylsulfamoyl)-ethyl]-amide. The title compound was obtained as its trifluoroacetate in form of a colorless amorphous material.

Workup

  1. washwashed with 3 ml of a saturated NaHCO3-solution
  2. dry with materialThe organic phase was dried over anhydrous MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customFinal purification by preparative RP-HPLC (CH3CN/H2O gradient+0.1% TFA)

Sources & evidence

ORD record
ord-db0c136803164f7aa359c9a7139ab805
Source dataset
uspto-grants-2012_01
Patent number
US08088925B2

Reaction notes

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