Water → HCID 67244766, compound

HRID 1753739Notes

Reaction equation

HRID 1753739 reaction equation
[H-].[Na+].[F:3][CH:4]([F:40])[C:5]1[CH:9]=[C:8]([CH:10]([F:12])[F:11])[N:7]([CH2:13][C:14]([N:16]2[CH2:21][CH2:20][CH:19]([C:22]3[S:23][CH:24]=[C:25]([C:27]4[CH2:31][CH:30]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=5[CH2:38]Cl)[O:29][N:28]=4)[N:26]=3)[CH2:18][CH2:17]2)=[O:15])[N:6]=1.O.ClCCl.[CH3:45][O:46][CH2:47][CH2:48][OH:49]>>[F:3][CH:4]([F:40])[C:5]1[CH:9]=[C:8]([CH:10]([F:12])[F:11])[N:7]([CH2:13][C:14]([N:16]2[CH2:21][CH2:20][CH:19]([C:22]3[S:23][CH:24]=[C:25]([C:27]4[CH2:31][CH:30]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=5[CH2:38][O:49][CH2:48][CH2:47][O:46][CH3:45])[O:29][N:28]=4)[N:26]=3)[CH2:18][CH2:17]2)=[O:15])[N:6]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 80192-Methoxyethanol2×HCID 24758Sodium hydrideHCID 672421852-[3,5-Bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(chloromethyl)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone

Product 1

HCID 67244766HCID 67244766, compound

Procedure

2-Methoxyethanol (1.5 ml) was admixed at room temperature with sodium hydride (60%, 17 mg) and then stirred at room temperature for 2 hours. To this mixture was added dropwise a solution of 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(chloromethyl)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone (0.20 g) in 2-methoxyethanol (1.5 g), and the mixture was then stirred at room temperature for 16 hours. Subsequently, the reaction mixture was admixed with water and dichloromethane. The organic extracts were dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by chromatography. This gave 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-{4-[4-(5-{2-[(2-methoxyethoxy)methyl]phenyl}-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazol-2-yl]piperidin-1-yl}ethanone (0.11 g).

Workup

  1. stirringthe mixture was then stirred at room temperature for 16 hours
  2. dry with materialThe organic extracts were dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-8d2384cce153472bb9779457dcda55a8
Source dataset
uspto-grants-2015_10
Patent number
US09167821B2

Reaction notes

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