Ethanol → HCID 20801191, compound

HRID 1071685Notes

Reaction equation

HRID 1071685 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[O:11][N:10]=[C:9]([CH2:12][N:13]3[C:21]4[C:16](=[CH:17][C:18]([C:22]([OH:24])=[O:23])=[CH:19][CH:20]=4)[CH:15]=[C:14]3[C:25](=[O:36])[NH:26][CH:27]3[CH2:32][CH2:31][N:30]([CH:33]([CH3:35])[CH3:34])[CH2:29][CH2:28]3)[CH:8]=2)=[CH:4][CH:3]=1.[CH3:37][CH2:38]O.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH2:37]([O:23][C:22]([C:18]1[CH:17]=[C:16]2[C:21](=[CH:20][CH:19]=1)[N:13]([CH2:12][C:9]1[CH:8]=[C:7]([C:5]3[S:6][C:2]([Cl:1])=[CH:3][CH:4]=3)[O:11][N:10]=1)[C:14]([C:25](=[O:36])[NH:26][CH:27]1[CH2:32][CH2:31][N:30]([CH:33]([CH3:34])[CH3:35])[CH2:29][CH2:28]1)=[CH:15]2)=[O:24])[CH3:38]

Participants

6

Reactant 3

HCID 702EthanolHCID 10868DicyclohexylcarbodiimideHCID 22394458HCID 22394458, compound

Product 1

HCID 20801191HCID 20801191, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.6 g 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-2-(1-isopropyl-piperidin-4-ylcarbamoyl)-1H-indole-5-carboxylic acid in 10 ml DMF sequentially 0.4 ml EtOH, 110 mg DMAP and 256 mg DCC were added and the reaction mixture was stirred for 16 h at room temperature. The precipitate was then filtered off and the filtrate was concentrated and purified by chromatography on silica gel eluting with DCM/MeOH/AcOH/H2O 95:3:0.5:0.5. The fractions containing the product were collected and the solvent evaporated under reduced pressure.

Workup

  1. filtrationThe precipitate was then filtered off
  2. concentrationthe filtrate was concentrated
  3. custompurified by chromatography on silica gel eluting with DCM/MeOH/AcOH/H2O 95:3:0.5:0.5
  4. additionThe fractions containing the product
  5. customwere collected
  6. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-e4f721e85f8f41ea83c061866e13f712
Source dataset
uspto-grants-2005_06
Patent number
US06906084B2

Reaction notes

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