Pyridine → HCID 86717530, compound

HRID 712070Notes

Reaction equation

HRID 712070 reaction equation
[OH:1][CH2:2][C@@H:3]1[O:8][CH2:7][C@@H:6]([N:9]2[C:13]3=[C:14]4[S:20][CH:19]=[CH:18][C:15]4=[N:16][CH:17]=[C:12]3[N:11]=[C:10]2[C@@H:21]([OH:23])[CH3:22])[CH2:5][CH2:4]1.N1C=CC=CC=1.[C:30]1([CH3:40])[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:40][C:30]1[CH:35]=[CH:34][C:33]([S:36]([O:1][CH2:2][C@H:3]2[CH2:4][CH2:5][C@H:6]([N:9]3[C:13]4=[C:14]5[S:20][CH:19]=[CH:18][C:15]5=[N:16][CH:17]=[C:12]4[N:11]=[C:10]3[C@@H:21]([OH:23])[CH3:22])[CH2:7][O:8]2)(=[O:38])=[O:37])=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 86717529HCID 86717529, compound

Product 1

HCID 86717530HCID 86717530, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (1S)-1-{1-[(3S,6R)-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]-1H-imidazo[4,5-d]thieno[3,2-b]pyridin-2-yl}ethanol (48.0 mg, 0.144 mmol) in methylene chloride (2.09 mL) and pyridine (70.4 μL, 0.871 mmol) was added p-toluenesulfonyl chloride (35.0 mg, 0.184 mmol) and 4-dimethylaminopyridine (1.1 mg, 0.0092 mmol). The reaction mixture was stirred at 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 as white solid (42 mg, 60%). LCMS calculated for C23H26N3O5S2 (M+H)+: m/z=488.1. Found: 488.1.

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-a98776782e38489281c39b441627377d
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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