Diisopropylethylamine → 3-chloro-5-cyanobenzyl 4-(5-(1H-1,2,3-triazol-4-yl)pentanamido)piperidine-1-carboxylate

HRID 1480489Notes

Reaction equation

HRID 1480489 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]#[N:20])[CH:16]=[C:15]([Cl:21])[CH:14]=2)=[O:10])[CH2:5][CH2:4]1.CCN(C(C)C)C(C)C.[NH:31]1[CH:35]=[C:34]([CH2:36][CH2:37][CH2:38][CH2:39][C:40](Cl)=[O:41])[N:33]=[N:32]1>C(Cl)Cl>[NH:31]1[CH:35]=[C:34]([CH2:36][CH2:37][CH2:38][CH2:39][C:40]([NH:2][CH:3]2[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]3[CH:18]=[C:17]([C:19]#[N:20])[CH:16]=[C:15]([Cl:21])[CH:14]=3)=[O:10])[CH2:5][CH2:4]2)=[O:41])[N:33]=[N:32]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 867227043-chloro-5-cyanobenzyl 4-aminopiperidine-1-carboxylate HCl saltHCID 1785211415-(1H-1,2,3-triazol-4-yl)pentanoyl chloride

Product 1

HCID 1785099033-chloro-5-cyanobenzyl 4-(5-(1H-1,2,3-triazol-4-yl)pentanamido)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a suspension of 3-chloro-5-cyanobenzyl 4-aminopiperidine-1-carboxylate hydrochloride salt (195 mg, 0.591 mmol) in DCM (5 mL) at RT under nitrogen was added Huenig's Base (0.206 mL, 1.182 mmol). 5-(1H-1,2,3-Triazol-4-yl)pentanoyl chloride (111 mg, 0.591 mmol) in DCM (2 mL) was then added and the reaction mixture stirred for 20 hours. The reaction mixture was diluted with DCM and washed with a 10% solution of citric acid, a saturated solution of brine and the organic portion was then dried over MgSO4, filtered and concentrated under reduced pressure. Purification was carried out by chromatography on silica using 0-10% MeOH in DCM to afford the title product.

Workup

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

Sources & evidence

ORD record
ord-3d67ef07cfcc45efb90285c3220196e1
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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