HCID 68380159, compound → HCID 68324157, compound

HRID 573658Notes

Reaction equation

HRID 573658 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[CH:17]=[C:16]([CH3:18])[N:15]=[C:14]3[S:19][C:20]([C:30]#[C:31][CH2:32][N:33]4[CH2:38][CH2:37][O:36][CH2:35][CH2:34]4)=[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=4)[C:13]=23)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1>[Pd].C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[CH:17]=[C:16]([CH3:18])[N:15]=[C:14]3[S:19][C:20]([CH2:30][CH2:31][CH2:32][N:33]4[CH2:34][CH2:35][O:36][CH2:37][CH2:38]4)=[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=4)[C:13]=23)(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 68380159HCID 68380159, compound

Product 1

HCID 68324157HCID 68324157, compoundYield 27.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-chloro-N-{6-methyl-3-[3-(methyloxy)phenyl]-2-[3-(4-morpholinyl)-1-propyn-1-yl]thieno[2,3-b]pyridin-4-yl}benzenesulfonamide (Example 86) (6.8 mg, 0.012 mmol) and palladium on carbon (2.55 mg, 2.394 μmol) in ethanol (2.0 mL) was stirred under an atmosphere of hydrogen at RT for 20 h. The mixture was then filtered through celite, washing with ethanol, and evaporated to dryness. The residue was purified on silica, eluting with a gradient of 0-10% MeOH in DCM to afford the title compound (1.9 mg). 1H NMR (MeOD, 400 MHz) δ ppm: 1.76 (2H, m), 2.27-2.40 (6H, m), 2.54 (3H, s), 2.69 (2H, m), 3.61 (4H, m), 3.84 (3H, s), 6.76-6.81 (2H, m), 7.04-7.10 (1H, m), 7.27 (1H, s), 7.39-7.48 (3H, m), 7.52-7.60 (2H, m).

Workup

  1. filtrationThe mixture was then filtered through celite
  2. washwashing with ethanol
  3. customevaporated to dryness
  4. customThe residue was purified on silica
  5. washeluting with a gradient of 0-10% MeOH in DCM

Sources & evidence

ORD record
ord-dd33b9d39cde4825b8d7f3efd074e3d7
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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