Methanesulfonyl chloride → HCID 86671852, compound

HRID 573598Notes

Reaction equation

HRID 573598 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[CH:8]=[C:9]([S:13]([NH:16][C:17]2[CH:22]=[C:21]([CH3:23])[N:20]=[C:19]3[S:24][C:25]([C:35]#[C:36][CH2:37][OH:38])=[C:26]([C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[CH:28]=4)[C:18]=23)(=[O:15])=[O:14])[CH:10]=[CH:11][CH:12]=1.CCN(C(C)C)C(C)C>C1COCC1>[CH3:1][S:2]([O:38][CH2:37][C:36]#[C:35][C:25]1[S:24][C:19]2=[N:20][C:21]([CH3:23])=[CH:22][C:17]([NH:16][S:13]([C:9]3[CH:10]=[CH:11][CH:12]=[C:7]([Cl:6])[CH:8]=3)(=[O:15])=[O:14])=[C:18]2[C:26]=1[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([O:33][CH3:34])[CH:28]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 68380182HCID 68380182, compound

Product 1

HCID 86671852HCID 86671852, compoundYield 28.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methane sulfonyl chloride (7.87 μl, 0.101 mmol) was added to a mixture of 3-chloro-N-{2-(3-hydroxy-1-propyn-1-yl)-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}benzenesulfonamide (Example 85) (42 mg, 0.084 mmol) and Hunig's base (17.64 μl, 0.101 mmol) in THF (395 μl) and the mixture stirred at 0° C. The mixture was slowly allowed to warm to RT, with stirring, for 2 h. The mixture was then evaporated to dryness and the residue purified on silica, eluting with a gradient of 0-100% ethyl acetate in cyclohexane, to afford the title compound (14 mg). LCMS (A) m/z: 517 [M+1]+ (displacement of OSO2Me by methanol), Rt 1.45 min (acidic).

Workup

  1. temperatureto warm to RT
  2. stirringwith stirring, for 2 h
  3. customThe mixture was then evaporated to dryness
  4. customthe residue purified on silica
  5. washeluting with a gradient of 0-100% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-5748f652bff14b0499d8c682721093a7
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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