Diisopropylethylamine → HCID 25124583, compound

HRID 872007Notes

Reaction equation

HRID 872007 reaction equation
Cl[C:2]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][N:12]([CH:21]3[CH2:23][CH2:22]3)[C:13]([C@@H:15]3[O:20][CH2:19][CH2:18][NH:17][CH2:16]3)=[O:14])=[CH:8][CH:9]=2)[N:4]([CH2:24][CH2:25][CH2:26][O:27][CH3:28])[CH:3]=1.C(N(C(C)C)CC)(C)C>C(O)C.[C].[Pd]>[CH:21]1([N:12]([CH2:11][C:7]2[CH:6]=[C:5]3[C:10]([CH:2]=[CH:3][N:4]3[CH2:24][CH2:25][CH2:26][O:27][CH3:28])=[CH:9][CH:8]=2)[C:13]([C@@H:15]2[O:20][CH2:19][CH2:18][NH:17][CH2:16]2)=[O:14])[CH2:22][CH2:23]1

Participants

5

Reactant 2

HCID 81531DiisopropylethylamineHCID 59494521HCID 59494521, compound

Product 1

HCID 25124583HCID 25124583, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

10% Palladium-carbon (20 mg) was added to a solution of (2R)—N-{[3-chloro-1-(3-methoxypropyl)-1H-indol-6-yl]methyl}-N-cyclopropylmorpholin-2-carboxamide (67 mg) and diisopropylethylamine (43 mg) in ethanol (3 ml) and the mixture was stirred under hydrogen atmosphere at room temperature for 8 hours. Insoluble materials were filtered and the filtrate was concentrated in vacuo. The resulted residue was dissolved in ethyl acetate, washed with a saturated aqueous solution of sodium bicarbonate and saturated brine successively, dried over magnesium sulfate and concentrated in vacuo. The resulted residue was purified with NH-silica gel column chromatography (eluting solvent: ethyl acetate to ethyl acetate/methanol=10/1) to give (2R)—N-cyclopropyl-N-{[1-(3-methoxypropyl)-1H-indol-6-yl]methyl}morpholin-2-carboxamide (53 mg) as a colorless oil.

Workup

  1. filtrationInsoluble materials were filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThe resulted residue was dissolved in ethyl acetate
  4. washwashed with a saturated aqueous solution of sodium bicarbonate and saturated brine successively
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resulted residue was purified with NH-silica gel column chromatography (eluting solvent: ethyl acetate to ethyl acetate/methanol=10/1)

Sources & evidence

ORD record
ord-daaeb17bb4764ababadc79c5ef620882
Source dataset
uspto-grants-2015_03
Patent number
US08975252B2

Reaction notes

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