Diisopropylethylamine → HCID 178427909, compound

HRID 1044341Notes

Reaction equation

HRID 1044341 reaction equation
[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.Cl.[OH:14][C@@H:15]1[CH2:20][CH2:19][C@H:18]([N:21]2[CH2:25][CH2:24][C:23]3([CH2:30][CH2:29][CH2:28][NH:27][CH2:26]3)[C:22]2=[O:31])[CH2:17][CH2:16]1.CCN(C(C)C)C(C)C>C(Cl)Cl.C(OCC)(=O)C>[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([S:8]([N:27]2[CH2:28][CH2:29][CH2:30][C:23]3([C:22](=[O:31])[N:21]([C@H:18]4[CH2:17][CH2:16][C@@H:15]([OH:14])[CH2:20][CH2:19]4)[CH2:25][CH2:24]3)[CH2:26]2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 5227343-Chloro-2-methylbenzenesulfonyl chlorideHCID 178479651HCID 178479651, compound

Product 1

HCID 178427909HCID 178427909, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-chloro-2-methylbenzenesulfonyl chloride (0.050 g, 0.22 mmol) in CH2Cl2 (1.0 mL) was slowly added to a mixture of 2-(cis-4-hydroxycyclohexyl)-2,7-diazaspiro[4.5]decan-1-one hydrochloride (0.060 g, 0.2 mmol) and DIPEA (0.10 mL, 0.6 mmol) in CH2Cl2 (1.0 mL) at 0° C. and the reaction was stirred for 1 h. The mixture was diluted with ethyl acetate and then washed with diluted HCl, water and brine, dried and concentrated. The product was purified by CombiFlash eluted with CH2Cl2/EtOAc. LC-MS: 441.2/443.2 (M+H)+.

Workup

  1. washwashed with diluted HCl, water and brine
  2. customdried
  3. concentrationconcentrated
  4. customThe product was purified by CombiFlash
  5. washeluted with CH2Cl2/EtOAc

Sources & evidence

ORD record
ord-7b04e2a6ed784d738a1e8df6afe5582b
Source dataset
uspto-grants-2013_10
Patent number
US08563570B2

Reaction notes

Loading…