HCID 46897675, compound → HCID 46896411, compound

HRID 1097547Notes

Reaction equation

HRID 1097547 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:42]([NH:44][S:45](=[O:50])(=[O:49])[N:46]([CH3:48])[CH3:47])=[O:43])=[CH:12][C:13]=3[N:14]3[CH2:20][C:19]([C:21]([N:23]4[CH2:27][C:26]56[CH2:32][N:33]([CH3:35])[CH2:34][C:25]5([CH2:30][N:29]([CH3:31])[CH2:28]6)[CH2:24]4)=[O:22])=[CH:18][C:17]4[CH:36]=[C:37]([O:40][CH3:41])[CH:38]=[CH:39][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[Pd]>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:42]([NH:44][S:45](=[O:49])(=[O:50])[N:46]([CH3:48])[CH3:47])=[O:43])=[CH:12][C:13]=3[N:14]3[CH2:20][CH:19]([C:21]([N:23]4[CH2:27][C:26]56[CH2:28][N:29]([CH3:31])[CH2:30][C:25]5([CH2:34][N:33]([CH3:35])[CH2:32]6)[CH2:24]4)=[O:22])[CH2:18][C:17]4[CH:36]=[C:37]([O:40][CH3:41])[CH:38]=[CH:39][C:16]=4[C:15]=23)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 46897675HCID 46897675, compound

Product 1

HCID 46896411HCID 46896411, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd/C (4 mg, 4 μmol) was added to a suspension of 13-cyclohexyl-N-(dimethylsulfamoyl)-6-((7,10-dimethyl-3,7,10-triazatricyclo[3.3.3.01,5]undec-3-yl)carbonyl)-3-methoxy-7H-indolo[2,1-a][2]benzazepine-10-carboxamide (Example 15) (6.0 mg, 8.6 μmol) in MeOH (2 mL). The reaction mixture was vacuum flushed with N2, and then with H2 and stirred under a H2 balloon at rt for 16 h. The reaction mixture was filtered through celite, and concentrated to yield 13-cyclohexyl-N-(dimethylsulfamoyl)-6-((7,10-dimethyl-3,7,10-triazatricyclo[3.3.3.01,5]undec-3-yl)carbonyl)-3-methoxy-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxamide (3.1 mg, 4.2 μmol, 49% yield) as an off white solid. LCMS: m/e 703 (M+H)+. LCMS retention time: 2.35 min. (Column: Phenomenex-Luna 3.0×50 mm S10. Solvent A=90% Water: 10% Methanol: 0.1% TFA. Solvent B=10% Water: 90% Methanol: 0.1% TFA. Start % B=0. Final % B=100. Gradient Time=3 min. Flow Rate=4 mL/min).

Workup

  1. customflushed with N2
  2. filtrationThe reaction mixture was filtered through celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-87f136a3882b4bdb8a67430be61263fa
Source dataset
uspto-grants-2012_03
Patent number
US08143244B2

Reaction notes

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