Methanesulfonyl chloride → HCID 73776917, compound

HRID 712119Notes

Reaction equation

HRID 712119 reaction equation
[NH2:1][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.C(N(CC)C(C)C)(C)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>CO>[OH:23][C@@H:21]([C:10]1[N:9]([C@@H:6]2[CH2:7][O:8][C@@H:3]([CH2:2][NH:1][S:34]([CH3:33])(=[O:36])=[O:35])[CH2:4][CH2:5]2)[C:13]2=[C:14]3[S:20][CH:19]=[CH:18][C:15]3=[N:16][CH:17]=[C:12]2[N:11]=1)[CH3:22]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chloride2×HCID 81531DiisopropylethylamineHCID 86717570HCID 86717570, compound

Product 1

HCID 73776917HCID 73776917, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of (1R)-1-{1-[(3S,6R)-6-(aminomethyl)tetrahydro-2H-pyran-3-yl]-1H-imidazo[4,5-d]thieno[3,2-b]pyridin-2-yl}ethanol (11 mg, 0.033 mmol) in methanol (0.5 mL) was added N,N-diisopropylethylamine (17 μL, 0.099 mmol) and methanesulfonyl chloride (2.8 μL, 0.036 mmol). After stirring for 0.5 h, another equivalent of methanesulfonyl chloride was added. After stirring for 20 min, The reaction solution was 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 30 mL/min) to give the desired product (5 mg, 37%). LCMS calculated for C17H23N4O4S2 (M+H)+: m/z=411.1. Found: 411.1.

Workup

  1. stirringAfter stirring for 20 min
  2. custompurified with prep-LCMS (XBridge C18 column
  3. washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 30 mL/min)

Sources & evidence

ORD record
ord-a426ed0d35a643d6941fcd2b85058ce4
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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