Azetidine → HCID 59295932, compound

HRID 2233382Notes

Reaction equation

HRID 2233382 reaction equation
Cl[S:2]([C:5]1[CH:14]=[C:13]2[C:8]([C:9]([C:16]([OH:18])=[O:17])=[CH:10][NH:11][C:12]2=[O:15])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[NH:19]1[CH2:22][CH2:21][CH2:20]1.C(N(C(C)C)CC)(C)C>O1CCCC1.C(#N)C>[N:19]1([S:2]([C:5]2[CH:14]=[C:13]3[C:8]([C:9]([C:16]([OH:18])=[O:17])=[CH:10][NH:11][C:12]3=[O:15])=[CH:7][CH:6]=2)(=[O:4])=[O:3])[CH2:22][CH2:21][CH2:20]1

Participants

6

Reactant 3

HCID 10422AzetidineHCID 81531DiisopropylethylamineHCID 59295966HCID 59295966, compound

Product 1

HCID 59295932HCID 59295932, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

7-(Chlorosulfonyl)-1-oxo-1,2-dihydroisoquinoline-4-carboxylic acid (1 g) was added to azetidine (0.7 ml) and diisopropylethylamine (0.4 ml) in tetrahydrofuran (5 ml) and acetonitrile (5 ml) and the mixture was stirred for 72 h then evaporated. The solid was crystallised from methanol then hydrochloric acid was added to acidify the mixture, which was filtered to yield 7-(azetidin-1-ylsulfonyl)-1-oxo-1,2-dihydroisoquinoline-4-carboxylic acid as a white solid.

Workup

  1. customthen evaporated
  2. customThe solid was crystallised from methanol
  3. additionhydrochloric acid was added
  4. filtrationwas filtered

Sources & evidence

ORD record
ord-b06bff156fb343edbd1c350daec987b9
Source dataset
uspto-grants-2010_05
Patent number
US07709500B2

Reaction notes

Loading…