Hydrochloric Acid → (S)-2,2-Difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)-1-(2-(5-((pyridin-3-yloxy)methyl)isoxazol-3-yl)pyrrolidin-1-yl)ethanone hydrochloride monohydrate

HRID 710070Notes

Reaction equation

HRID 710070 reaction equation
CC[O:3]C(C)=O.[F:7][C:8]([F:40])([C:29]1([OH:39])[CH2:34][C:33]([CH3:36])([CH3:35])[CH2:32][C:31]([CH3:38])([CH3:37])[CH2:30]1)[C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16]1[CH:20]=[C:19]([CH2:21][O:22][C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[O:18][N:17]=1)=[O:10].[ClH:41]>CCCCC>[OH2:3].[ClH:41].[F:40][C:8]([F:7])([C:29]1([OH:39])[CH2:30][C:31]([CH3:38])([CH3:37])[CH2:32][C:33]([CH3:36])([CH3:35])[CH2:34]1)[C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16]1[CH:20]=[C:19]([CH2:21][O:22][C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[O:18][N:17]=1)=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 73672050Setafrastat

Product 1

HCID 86706783(S)-2,2-Difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)-1-(2-(5-((pyridin-3-yloxy)methyl)isoxazol-3-yl)pyrrolidin-1-yl)ethanone hydrochloride monohydrate

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

To an AcOEt (50 ml) solution of Compound 40 (2.24 g) obtained in Example 2, HCl (50 ml, 4.0 N in AcOEt) was added and the mixture was stirred at room temperature for 15 hours, and after adding pentane (140 ml), the mixture was stirred for 8 days. The residue obtained by concentrating the reaction mixture was recrystallized (MeOH/Et2O) to give the titled compound (2.23 g, colorless powder.)

Workup

  1. stirringthe mixture was stirred for 8 days
  2. customThe residue obtained
  3. concentrationby concentrating the reaction mixture
  4. customwas recrystallized (MeOH/Et2O)

Sources & evidence

ORD record
ord-63cb76eccbd6493b9ed8108ffee04d80
Source dataset
uspto-grants-2015_11
Patent number
US09181229B2

Reaction notes

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