Sodium Bicarbonate → N-cyclopropylmorpholine-2-carboxamide

HRID 872008Notes

Reaction equation

HRID 872008 reaction equation
[CH:1]1([N:4]([CH2:20][C:21]2[CH:29]=[C:28]3[C:24]([CH:25]=[CH:26][N:27]3[CH2:30][CH2:31][CH2:32][O:33][CH3:34])=[CH:23][C:22]=2[F:35])[C:5]([C@@H:7]2[O:12][CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8]2)=[O:6])[CH2:3][CH2:2]1.C(=O)(O)[O-].[Na+]>ClCCl.[Br-].[Zn+2].[Br-]>[CH:1]1([N:4]([CH2:20][C:21]2[CH:29]=[C:28]3[C:24]([CH:25]=[CH:26][N:27]3[CH2:30][CH2:31][CH2:32][O:33][CH3:34])=[CH:23][C:22]=2[F:35])[C:5]([C@@H:7]2[O:12][CH2:11][CH2:10][NH:9][CH2:8]2)=[O:6])[CH2:2][CH2:3]1.[CH:1]1([NH:4][C:5]([CH:7]2[O:12][CH2:11][CH2:10][NH:9][CH2:8]2)=[O:6])[CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 59494410tert-butyl(2R)-2-[(cyclopropyl{[5-fluoro-1-(3-methoxypropyl)-1H-indol-6-yl]methyl}amino)carbonyl]morpholin-4-carboxylate

Product 2

HCID 57937375N-cyclopropylmorpholine-2-carboxamideHCID 59494153(2R)-N-cyclopropyl-N-{[5-fluoro-1-(3-methoxypropyl)-1H-indol-6-yl]methyl}morpholin-2-carboxamide

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 6344DichloromethaneSolvent

Procedure

Zinc bromide (160 mg) was added to a solution of tert-butyl(2R)-2-[(cyclopropyl{[5-fluoro-1-(3-methoxypropyl)-1H-indol-6-yl]methyl}amino)carbonyl]morpholin-4-carboxylate (150 mg) in dichloromethane (3 ml) and the mixture was stirred at room temperature for 10 hours. A saturated aqueous solution of sodium bicarbonate was added to the reaction mixture under ice-cooling, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated in vacuo. The resulted residue was purified with HPLC MS to give (2R)—N-cyclopropyl-N-{[5-fluoro-1-(3-methoxypropyl)-1H-indol-6-yl]methyl}morpholin-2-carboxamide (50 mg) and (2R)—N-{[3-tert-butyl-5-fluoro-1-methoxypropyl)-1H-indol-6-yl]methyl}-N-cyclopropylmorpholin-2-carboxamide (50 mg) as a colorless oil.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulted residue was purified with HPLC MS

Sources & evidence

ORD record
ord-689db8a9c8854ef49b6285debfcf9be1
Source dataset
uspto-grants-2015_03
Patent number
US08975252B2

Reaction notes

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