Acetonitrile → N-Isopropyl-4-methoxy-3-(3-methoxy-propoxy)-N-((3S*,4S*)-4-piperidin-1-ylmethyl-pyrrolidin-3-ylmethyl)-benzamide

HRID 1158339Notes

Reaction equation

HRID 1158339 reaction equation
C(OC([N:8]1[CH2:12][C@@H:11]([CH2:13][N:14]([CH:31]([CH3:33])[CH3:32])[C:15](=[O:30])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:17]=2)[C@H:10]([CH:34]=O)[CH2:9]1)=O)(C)(C)C.[NH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1.CC#N.O.CC#N>O>[CH:31]([N:14]([CH2:13][C@H:11]1[C@H:10]([CH2:34][N:36]2[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)[CH2:9][NH:8][CH2:12]1)[C:15](=[O:30])[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:17]=1)([CH3:33])[CH3:32]

Participants

6

Reactant 4

HCID 6342Acetonitrile2×HCID 8082PiperidineHCID 18373917Acetonitrile--water (1/1)HCID 59512275(3S*,4R*)-3-formyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 11851727N-Isopropyl-4-methoxy-3-(3-methoxy-propoxy)-N-((3S*,4S*)-4-piperidin-1-ylmethyl-pyrrolidin-3-ylmethyl)-benzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound is prepared analogously as described in Example 5 from (3S*,4R*)-3-formyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester and piperidine. MS (LC-MS): 462.1 [M+H]+; tR (HPLC, Macherey-Nagel Nucleosil C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/3 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 mL/min): 3.74 min.

Workup

  1. custom3.74 min.

Sources & evidence

ORD record
ord-6a1c2fabfed84dafa4cf67e3f1fe3299
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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