2,6-Dimethylmorpholine, cis- → 6-Chloro-4-(5-{[(2R,6S)-2,6-dimethyl-4-morpholinyl]methyl}-1,3-oxazol-2-yl)-1-(phenylsulfonyl)-1H-indazole

HRID 520558Notes

Reaction equation

HRID 520558 reaction equation
Br[CH2:2][C:3]1[O:7][C:6]([C:8]2[CH:16]=[C:15]([Cl:17])[CH:14]=[C:13]3[C:9]=2[CH:10]=[N:11][N:12]3[S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[N:5][CH:4]=1.[CH3:27][C@H:28]1[O:33][C@@H:32]([CH3:34])[CH2:31][NH:30][CH2:29]1>ClCCl>[Cl:17][C:15]1[CH:14]=[C:13]2[C:9]([CH:10]=[N:11][N:12]2[S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:19])=[O:20])=[C:8]([C:6]2[O:7][C:3]([CH2:2][N:30]3[CH2:29][C@H:28]([CH3:27])[O:33][C@H:32]([CH3:34])[CH2:31]3)=[CH:4][N:5]=2)[CH:16]=1

Participants

4

Reactant 2

HCID 6415002,6-Dimethylmorpholine, cis-HCID 595647134-[5-(Bromomethyl)-1,3-oxazol-2-yl]-6-chloro-1-(phenylsulfonyl)-1H-indazole

Product 1

HCID 595647046-Chloro-4-(5-{[(2R,6S)-2,6-dimethyl-4-morpholinyl]methyl}-1,3-oxazol-2-yl)-1-(phenylsulfonyl)-1H-indazoleYield 96.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[5-(Bromomethyl)-1,3-oxazol-2-yl]-6-chloro-1-(phenylsulfonyl)-1H-indazole (0.580 g, 1.28 mmol) was dissolved in dichloromethane (5 ml) and (2R,6S)-2,6-dimethylmorpholine (0.317 ml, 2.56 mmol) added. The reaction mixture was stirred at RT for 3 h then the solvent removed under a stream of nitrogen. The resultant yellow solid was dissolved in dichloromethane (5 ml) and washed with water (2×2.5 ml). The layers were separated (hydrophobic frit) and the organic evaporated in vacuo to give the title compound as a pale yellow solid (0.60 g).

Workup

  1. customthe solvent removed under a stream of nitrogen
  2. dissolutionThe resultant yellow solid was dissolved in dichloromethane (5 ml)
  3. washwashed with water (2×2.5 ml)
  4. customThe layers were separated (hydrophobic frit)
  5. customthe organic evaporated in vacuo

Sources & evidence

ORD record
ord-191cf21eafa64d67a4bea221baedfc4e
Source dataset
uspto-grants-2016_05
Patent number
US09326987B2

Reaction notes

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