Potassium Carbonate → HCID 58493994, compound

HRID 2360500Notes

Reaction equation

HRID 2360500 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:41][OH:42])[C:8]([O:39][CH3:40])=[C:9]([NH:11][C:12]([C:14]2[N:15]([CH3:38])[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][CH2:34][N:33]3[CH3:37])=[O:31])[CH2:26][CH2:25]2)=[O:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[C:1]([C:5]1[CH:6]=[C:7]([CH:41]=[O:42])[C:8]([O:39][CH3:40])=[C:9]([NH:11][C:12]([C:14]2[N:15]([CH3:38])[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][CH2:34][N:33]3[CH3:37])=[O:31])[CH2:26][CH2:25]2)=[O:13])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 159087TriacetoxyperiodinaneHCID 58493931HCID 58493931, compound

Product 1

HCID 58493994HCID 58493994, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

200 mg (S)-1-methyl-7-[4-(1-methyl-pyrrolidine-2-carbonyl)-piperazin-1-ylmethyl]-1H-indole-2-carboxylic acid-(5-tert-butyl-3-hydroxymethyl-2-methoxy-phenyl)-amide are dissolved in 5 ml dichloromethane, cooled to 0° C. and combined with 167 mg 1,1-dihydro-1,1,1-triacetoxy-1,2-benziodoxol-3(1H)-one (Dess-Martin-Periodinane). The mixture is stirred for 12 hours, while being heated to ambient temperature. Then it is divided between dichloromethane and a 10% aqueous potassium carbonate solution. A solid is precipitated which is filtered off. The liquid phases are separated and the organic phase is dried on magnesium sulphate. The solvents are then eliminated in vacuo. The product thus obtained is further reacted directly.

Workup

  1. temperaturewhile being heated to ambient temperature
  2. customA solid is precipitated which
  3. filtrationis filtered off
  4. customThe liquid phases are separated
  5. customthe organic phase is dried on magnesium sulphate
  6. customThe product thus obtained
  7. customis further reacted directly

Sources & evidence

ORD record
ord-a17af7a3140544bbafc285aa72ee639f
Source dataset
uspto-grants-2014_04
Patent number
US08686022B2

Reaction notes

Loading…