Formaldehyde → HCID 46190615, compound

HRID 2360526Notes

Reaction equation

HRID 2360526 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:40][S:41]([CH3:44])(=[O:43])=[O:42])[C:8]([O:38][CH3:39])=[C:9]([NH:11][C:12]([C:14]2[N:15]([CH3:37])[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][C:17]=3[CH2:23][N:24]2[CH2:29][CH2:28][N:27]([C:30]([C@H:32]3[CH2:36][CH2:35][NH:34][CH2:33]3)=[O:31])[CH2:26][CH2:25]2)=[O:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:45]=O>CO.O.[Pd]>[C:1]([C:5]1[CH:6]=[C:7]([NH:40][S:41]([CH3:44])(=[O:43])=[O:42])[C:8]([O:38][CH3:39])=[C:9]([NH:11][C:12]([C:14]2[N:15]([CH3:37])[C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][C:17]=3[CH2:23][N:24]2[CH2:29][CH2:28][N:27]([C:30]([C@H:32]3[CH2:36][CH2:35][N:34]([CH3:45])[CH2:33]3)=[O:31])[CH2:26][CH2:25]2)=[O:13])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 712FormaldehydeHCID 58493941HCID 58493941, compound

Product 1

HCID 46190615HCID 46190615, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

100 mg of (S)-1-methyl-7-[4-(pyrrolidine-3-carbonyl)-piperazin-1-ylmethyl]-1H-indole-2-carboxylic acid (5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-amide are dissolved in 10 ml of methanol, combined with 14 μl of a 37% solution of formaldehyde in water and 20 mg of palladium on charcoal (10%) and hydrogenated for 4 hours at 4 bar. The catalyst is filtered off, the solvents are eliminated in vacuo and the residue is chromatographed on aluminium oxide (dichloromethane/methanol 95:5 to 80:20).

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe residue is chromatographed on aluminium oxide (dichloromethane/methanol 95:5 to 80:20)

Sources & evidence

ORD record
ord-96c914f7f59247458c38b398e78ca5e8
Source dataset
uspto-grants-2014_04
Patent number
US08686022B2

Reaction notes

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