Water → HCID 67439341, compound

HRID 1890276Notes

Reaction equation

HRID 1890276 reaction equation
C([O-])(O)=O.[Na+].[I:6]N1C(=O)CCC1=O.[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[C:22](C(O)=O)=[C:23]3[CH2:28][CH2:27][CH:26]([CH3:29])[N:24]3[N:25]=2)=[CH:17][CH:16]=1.O>CN(C)C=O>[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[C:22]([I:6])=[C:23]3[CH2:28][CH2:27][CH:26]([CH3:29])[N:24]3[N:25]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 120273N-IodosuccinimideHCID 516892Sodium BicarbonateHCID 674367222-(4-fluorophenyl)-6-methyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylic acid

Product 1

HCID 67439341HCID 67439341, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.1 g (36.9 mmol) of NaHCO3 and 2.8 g (12.3 mmol) of N-iodosuccinimide are added to a solution of 3.2 g (12.3 mmol) of 2-(4-fluorophenyl)-6-methyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylic acid in 25 ml of dimethylformamide. The reaction mixture is stirred at room temperature for 16 h, water is added and the precipitated solid is filtered off and dried. This gives 3.30 g of the desired product in a purity of 77% which are reacted further without further purification: (log P(HCOOH): 3.82); 1H-NMR (ppm): δ (DMSO-d6)=1.42 (d, 3H), 2.11-2.18 (m, 1H), 2.72-2.82 (m, 3H), 4.49 (m, 1H), 7.28 (dd, 2H), 7.79 (dd, 2H); LC-MS: m/z=343 [M+H]+.

Workup

  1. filtrationthe precipitated solid is filtered off
  2. customdried
  3. customThis gives 3.30 g of the desired product in a purity of 77% which are reacted further without further purification

Sources & evidence

ORD record
ord-ccb86a9f05cf488e801f341468650df9
Source dataset
uspto-grants-2013_08
Patent number
US08507472B2

Reaction notes

Loading…