Diisopropylethylamine → HCID 178425016, compound

HRID 1480462Notes

Reaction equation

HRID 1480462 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][CH2:8][C:9](Cl)=[O:10])[N:3]=[N:2]1.[NH2:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[CH:24]=2)=[O:20])[CH2:15][CH2:14]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][CH2:8][C:9]([NH:12][CH:13]2[CH2:14][CH2:15][N:16]([C:19]([O:21][CH2:22][C:23]3[CH:24]=[C:25]([CH3:30])[CH:26]=[C:27]([CH3:29])[CH:28]=3)=[O:20])[CH2:17][CH2:18]2)=[O:10])[N:3]=[N:2]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 867226873,5-Dimethylbenzyl 4-aminopiperidine-1-carboxylateHCID 178521140HCID 178521140, compound

Product 1

HCID 178425016HCID 178425016, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 4-(1H-1,2,3-triazol-4-yl)butanoic acid chloride in DCM (5 ml) at RT (168 mg, 0.967 mmol) was added 3,5-dimethylbenzyl 4-aminopiperidine-1-carboxylate (318 mg, 1.064 mmol) and Huenig's Base (0.338 mL, 1.934 mmol) and the reaction mixture was allowed to stir for 3 hrs. The reaction mixture was diluted with DCM and washed with a saturated solution of brine. The layers were separated and the organic portion 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 saturated solution of brine
  2. customThe layers were separated
  3. dry with materialthe organic portion dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification

Sources & evidence

ORD record
ord-b367eeb438974882ac037c6278518740
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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