Diisopropylethylamine → HCID 178426889, compound

HRID 1480483Notes

Reaction equation

HRID 1480483 reaction equation
Cl.[NH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([CH3:23])[CH:14]=2)=[O:10])[CH2:5][CH2:4]1.CCN(C(C)C)C(C)C.[NH:33]1[CH:37]=[C:36]([CH2:38][CH2:39][CH2:40][C:41](Cl)=[O:42])[N:35]=[N:34]1>C(Cl)Cl>[NH:33]1[CH:37]=[C:36]([CH2:38][CH2:39][CH2:40][C:41]([NH:2][CH:3]2[CH2:4][CH2:5][N:6]([C:9]([O:11][CH2:12][C:13]3[CH:18]=[C:17]([C:19]([F:22])([F:20])[F:21])[CH:16]=[C:15]([CH3:23])[CH:14]=3)=[O:10])[CH2:7][CH2:8]2)=[O:42])[N:35]=[N:34]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 902187333-Methyl-5-(trifluoromethyl)benzyl 4-aminopiperidine-1-carboxylate hydrochloride saltHCID 178521140HCID 178521140, compound

Product 1

HCID 178426889HCID 178426889, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred suspension of 3-methyl-5-(trifluoromethyl)benzyl 4-aminopiperidine-1-carboxylate hydrochloride salt (201 mg, 0.570 mmol) in DCM (5 mL) at RT under nitrogen was added Huenig's Base (0.199 mL, 1.140 mmol). 4-(1H-1,2,3,-triazol-4-yl)butanoyl chloride (99 mg, 0.570 mmol) in DCM (2 mL) was added and the reaction mixture stirred at RT for 2 hours. The reaction mixture was diluted with DCM and washed with a 10% solution of citric acid, and saturated brine solution, before the organic portion was dried over MgSO4, filtered and concentrated under reduced pressure. Purification was carried out by chromatography on silica using 0-10% MeOH in DCM as eluent to afford the title product;

Workup

  1. washwashed with a 10% solution of citric acid, and saturated brine solution, before the organic portion
  2. dry with materialwas dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification

Sources & evidence

ORD record
ord-b1c6e6a5dc464c6e81d6302649677db7
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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