Methanesulfonyl chloride → HCID 178505298, compound

HRID 711933Notes

Reaction equation

HRID 711933 reaction equation
[N+:1]([C:4]1[C:5]([NH:13][C@H:14]2[CH2:19][CH2:18][C@H:17]([CH2:20][OH:21])[CH2:16][CH2:15]2)=[C:6]2[S:12][CH:11]=[CH:10][C:7]2=[N:8][CH:9]=1)([O-:3])=[O:2].C(N(CC)C(C)C)(C)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>C(Cl)Cl.O>[CH3:31][S:32]([O:21][CH2:20][C@H:17]1[CH2:16][CH2:15][C@H:14]([NH:13][C:5]2[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=[C:7]3[CH:10]=[CH:11][S:12][C:6]=23)[CH2:19][CH2:18]1)(=[O:34])=[O:33]

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 178526780HCID 178526780, compound

Product 1

HCID 178505298HCID 178505298, compoundYield 61.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of {trans-4-[(6-nitrothieno[3,2-b]pyridin-7-yl)amino]cyclohexyl}methanol (0.26 g, 0.84 mmol) and N,N-diisopropylethylamine (0.30 mL, 1.7 mmol) in methylene chloride (3 mL) was added methanesulfonyl chloride (0.085 mL, 1.1 mmol). The resulting mixture was stirred at room temperature for 2 h. After diluting with water, the mixture was extracted with dichloromethane. The organic layers were concentrated and purified on silica gel (eluting with 0 to 70% EtOAc in hexanes) to give the desired product (0.2 g, 61%). LCMS calculated for C15H20N3O5S2 (M+H)+: m/z=386.1. Found: 386.0.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. concentrationThe organic layers were concentrated
  3. custompurified on silica gel (eluting with 0 to 70% EtOAc in hexanes)

Sources & evidence

ORD record
ord-26e8ad9edd714e45ab157cbd4ae2cb1c
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

Loading…