Potassium Carbonate → Methyl 1-{3-[2-[3-(phenylsulphonylamino)-phenyl]-2-hydroxy-ethylamino]-3-methyl-butyl}-1H-indole-5-carboxylate

HRID 2355247Notes

Reaction equation

HRID 2355247 reaction equation
C(O[CH:4](O)[C:5]([C:7]1[CH:8]=[C:9]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH:10]=[CH:11][CH:12]=1)=[O:6])C.[NH2:24][C:25]([CH3:42])([CH3:41])[CH2:26][CH2:27][N:28]1[C:36]2[C:31](=[CH:32][C:33]([C:37]([O:39][CH3:40])=[O:38])=[CH:34][CH:35]=2)[CH:30]=[CH:29]1.[BH4-].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(O)C.C(N(CC)CC)C.C(OCC)(=O)C>[C:17]1([S:14]([NH:13][C:9]2[CH:8]=[C:7]([CH:5]([OH:6])[CH2:4][NH:24][C:25]([CH3:42])([CH3:41])[CH2:26][CH2:27][N:28]3[C:36]4[C:31](=[CH:32][C:33]([C:37]([O:39][CH3:40])=[O:38])=[CH:34][CH:35]=4)[CH:30]=[CH:29]3)[CH:12]=[CH:11][CH:10]=2)(=[O:15])=[O:16])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 4311764Sodium borohydrideHCID 57429080N-[3-(2-ethoxy-2-hydroxyacetyl)-phenyl]-benzenesulphonamideHCID 68453514Methyl 1-(3-amino-3-methyl-butyl)-indole-5-carboxylate

Product 1

HCID 16659831Methyl 1-{3-[2-[3-(phenylsulphonylamino)-phenyl]-2-hydroxy-ethylamino]-3-methyl-butyl}-1H-indole-5-carboxylate

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

154 mg (0.46 mmol) N-[3-(2-ethoxy-2-hydroxyacetyl)-phenyl]-benzenesulphonamide (Component I) and 125 mg (0.48 mmol) methyl 1-(3-amino-3-methyl-butyl)-indole-5-carboxylate (Component IV) are dissolved in 10 ml of ethanol and combined with 4 drops of triethylamine. The reaction solution is heated to 80° C. for 17 hours. Then it is cooled to 0° C. and over a period of 2.5 hours 140 mg (3.7 mmol) sodium borohydride are added batchwise. The mixture is stirred for another hour at 0° C. and the reaction solution is then poured into a mixture of 20 ml of saturated aqueous potassium carbonate solution and 50 ml of ethyl acetate. After separation of the organic phase the aqueous phase is extracted with ethyl acetate. The combined organic phases are with washed saturated aqueous saline solution and dried on sodium sulphate. Then the solvent is eliminated in vacuo and the residue is chromatographed on silica gel (DCM/methanol=100:0:0→9:1).

Workup

  1. additionare added batchwise
  2. customAfter separation of the organic phase the aqueous phase
  3. extractionis extracted with ethyl acetate
  4. customdried on sodium sulphate
  5. customthe residue is chromatographed on silica gel (DCM/methanol=100:0:0→9:1)

Sources & evidence

ORD record
ord-939f452e2a78453f9dbf29b55708be13
Source dataset
uspto-grants-2010_07
Patent number
US07754756B2

Reaction notes

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