Tetrahydrofuran → HCID 9883721, compound

HRID 853856Notes

Reaction equation

HRID 853856 reaction equation
[O:1]=[C:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:12](Cl)(=[O:14])=[O:13])[CH:8]=2)[NH:3]1.C1COCC1.C(N(CC)C(C)C)(C)C.[CH3:30][O:31][CH2:32][C@H:33]1[CH2:37][CH2:36][CH2:35][NH:34]1>C(Cl)(Cl)Cl>[CH3:30][O:31][CH2:32][C@H:33]1[CH2:37][CH2:36][CH2:35][N:34]1[S:12]([C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[NH:3][C:2](=[O:1])[C:10]2=[O:11])(=[O:14])=[O:13]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 671216(2R)-2-(Methoxymethyl)pyrrolidineHCID 159089472,3-Dioxoindoline-5-sulfonyl chloride

Product 1

HCID 9883721HCID 9883721, compoundYield 63.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred cold suspension of 2,3-dioxo-2,3-dihydro-1H-indol-5-sulfonyl chloride (5.00 g, 20.4 mmol) in a 1:1 mixture of THF: CHCl3 (140 mL) was added dropwise, via syringe pump, a solution of N,N-diisopropylethylamine (7.11 mL, 40.8 mmol, 2 eq) and (R)-2-(Methoxymethyl)pyrrolidine (3.27 mL, 26.5 mmol, 1.3 eq) in CHCl3 (60 mL) over a period of 1.5 hours with cooling in an ice bath. After stirring an additional 1 h, the reaction was concentrated. The crude product was purified on Biotage KP silica gel eluting with 95/5 CH2Cl2/CH3OH followed by a second chromatography on silica gel eluting with EtOAc to give 4.21 g (63.8% ) of the title compound. NMR (400 MHz, DMSO-d6): consistent.

Workup

  1. concentrationthe reaction was concentrated
  2. customThe crude product was purified on Biotage KP silica gel eluting with 95/5 CH2Cl2/CH3OH

Sources & evidence

ORD record
ord-bc5f0eb7d2c64fc087ef60a71ad6554f
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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