Acetic Anhydride → HCID 24863632, compound

HRID 1804865Notes

Reaction equation

HRID 1804865 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([CH:14]([NH2:27])[CH2:15][N:16]3[C:20]([CH3:21])=[C:19]([Cl:22])[C:18]([C:23]([F:26])([F:25])[F:24])=[N:17]3)[CH2:10][CH2:9]2)=[CH:4][C:3]=1[O:28][CH3:29].[C:30](OC(=O)C)(=[O:32])[CH3:31]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([CH:14]([NH:27][C:30](=[O:32])[CH3:31])[CH2:15][N:16]3[C:20]([CH3:21])=[C:19]([Cl:22])[C:18]([C:23]([F:25])([F:26])[F:24])=[N:17]3)[CH2:10][CH2:9]2)=[CH:4][C:3]=1[O:28][CH3:29]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 68552689HCID 68552689, compound

Product 1

HCID 24863632HCID 24863632, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-(1-(4-chloro-3-methoxyphenyl)piperidin-4-yl)-2-(4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)ethanamine (49 mg, 0.109 mmol) in anhydrous DCM (1.5 mL) was treated with acetic anhydride (0.012 mL, 0.130 mmol) and DMAP (1.3 mg, 11 μmol), and the resultant mixture was stirred at RT for 1.5 h. After this time, the mixture was diluted with DCM (5 mL) and then washed sequentially with saturated NaHCO3 and brine. The organic extract was dried (MgSO4) and concentrated in vacuo to give N-(1-(1-(4-chloro-3-methoxyphenyl)piperidin-4-yl)-2-(4-chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)ethyl)acetamide (49 mg), which was used without further purification in the reaction below. LC-MS: 493.25, [M+H]+; tR=3.08 min (method b).

Workup

  1. washwashed sequentially with saturated NaHCO3 and brine
  2. extractionThe organic extract
  3. dry with materialwas dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bbc40e43a0f3461fa7d151ae0aecb2ff
Source dataset
uspto-grants-2013_01
Patent number
US08354432B2

Reaction notes

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