Pyridine → HCID 86717522, compound

HRID 712062Notes

Reaction equation

HRID 712062 reaction equation
[CH3:1][C:2]1[N:13]([C@@H:14]2[CH2:19][O:18][C@@H:17]([CH2:20][OH:21])[CH2:16][CH2:15]2)[C:5]2=[C:6]3[S:12][CH:11]=[CH:10][C:7]3=[N:8][CH:9]=[C:4]2[N:3]=1.N1C=CC=CC=1.[C:28]1([CH3:38])[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:38][C:28]1[CH:33]=[CH:32][C:31]([S:34]([O:21][CH2:20][C@H:17]2[CH2:16][CH2:15][C@H:14]([N:13]3[C:5]4=[C:6]5[S:12][CH:11]=[CH:10][C:7]5=[N:8][CH:9]=[C:4]4[N:3]=[C:2]3[CH3:1])[CH2:19][O:18]2)(=[O:36])=[O:35])=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 86717521HCID 86717521, compound

Product 1

HCID 86717522HCID 86717522, compoundYield 55.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of [(2R,5S)-5-(2-methyl-1H-imidazo[4,5-d]thieno[3,2-b]pyridin-1-yl)tetrahydro-2H-pyran-2-yl]methanol (60.1 mg, 0.198 mmol) in methylene chloride (2.3 mL) and pyridine (51 μL, 0.62 mmol) was added p-toluenesulfonyl chloride (38.7 mg, 0.203 mmol) and 4-dimethylaminopyridine (1.2 mg, 0.010 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature overnight. The reaction mixture was concentrated, diluted with methanol, and purified with prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min) to give the desired product (50 mg, 55%). LCMS calculated for C22H24N3O4S2 (M+H)+: m/z=458.1. Found: 458.1.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with methanol
  3. custompurified with prep-LCMS (XBridge C18 column
  4. washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min)

Sources & evidence

ORD record
ord-5223cc1119dd46c09cc22f672a02540d
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

Loading…