Chlorosuccinimide → HCID 58515969, compound

HRID 717834Notes

Reaction equation

HRID 717834 reaction equation
[CH:1]([NH:3][CH2:4][C:5]1[N:10]=[C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)[C:8]([C:24]([O:26][CH3:27])=[O:25])=[CH:7][CH:6]=1)=[O:2].[Cl:28]N1C(=O)CCC1=O>O1CCCC1>[Cl:28][C:6]1[CH:7]=[C:8]([C:24]([O:26][CH3:27])=[O:25])[C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[CH2:13][CH2:12]2)=[N:10][C:5]=1[CH2:4][NH:3][CH:1]=[O:2]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 58515972HCID 58515972, compound

Product 1

HCID 58515969HCID 58515969, compoundYield 106%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 4-{6-[(formylamino)methyl]-3-(methoxycarbonyl)pyridin-2-yl}piperazine-1-carboxylate (4.85 g, 0.0128 mol) and N-chlorosuccinimide (2.1 g, 15 mmol) was stirred in tetrahydrofuran (85 mL) at 50° C. for 16 hours. Evaporation and purification on silica gel using ethyl acetate in hexanes (0-80%) gave the desired compound (5.6 g, 100%). LCMS calculated for C18H26ClN4O5 (M+H)+: m/z=413.2. found: 412.9.

Workup

  1. customEvaporation and purification on silica gel

Sources & evidence

ORD record
ord-15be276ec7804644b56c7eaa060ff4cb
Source dataset
uspto-grants-2015_11
Patent number
US09193721B2

Reaction notes

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