2,6-Dimethylmorpholine, cis- → N-{6-Bromo-1-[(4-methylphenyl)sulfonyl]-1H-indazol-4-yl}-2-{[(2R,6S)-2,6-dimethyl-4-morpholinyl]methyl}-1,3-thiazole-4-carboxamide

HRID 1695738Notes

Reaction equation

HRID 1695738 reaction equation
[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][NH:4][CH2:3]1.[Br:9][C:10]1[CH:18]=[C:17]2[C:13]([CH:14]=[N:15][N:16]2[S:19]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[C:12]([NH:29][C:30]([C:32]2[N:33]=[C:34]([CH2:37]Cl)[S:35][CH:36]=2)=[O:31])[CH:11]=1>C(#N)C>[Br:9][C:10]1[CH:18]=[C:17]2[C:13]([CH:14]=[N:15][N:16]2[S:19]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[C:12]([NH:29][C:30]([C:32]2[N:33]=[C:34]([CH2:37][N:4]3[CH2:5][C@H:6]([CH3:8])[O:7][C@H:2]([CH3:1])[CH2:3]3)[S:35][CH:36]=2)=[O:31])[CH:11]=1

Participants

4

Reactant 2

HCID 6415002,6-Dimethylmorpholine, cis-HCID 58255773N-{6-Bromo-1-[(4-methylphenyl)sulfonyl]-1H-indazol-4-yl}-2-(chloromethyl)-1,3-thiazole-4-carboxamide

Product 1

HCID 58255797N-{6-Bromo-1-[(4-methylphenyl)sulfonyl]-1H-indazol-4-yl}-2-{[(2R,6S)-2,6-dimethyl-4-morpholinyl]methyl}-1,3-thiazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Acetonitrile (15 mL) and (2R,6S)-2,6-dimethylmorpholine (1.4 ml) were added to N-{6-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indazol-4-yl}-2-(chloromethyl)-1,3-thiazole-4-carboxamide (2 g) and the reaction mixture was refluxed for 3 h. On cooling a solid precipitated. The mixture was diluted with acetonitrile (15 ml) and the solid was collected by filtration, washing with acetonitrile. The solid was dried on the vacuum pump overnight to give title compound (1.86 g).

Workup

  1. temperaturethe reaction mixture was refluxed for 3 h
  2. temperatureOn cooling a solid
  3. customprecipitated
  4. additionThe mixture was diluted with acetonitrile (15 ml)
  5. filtrationthe solid was collected by filtration
  6. washwashing with acetonitrile
  7. customThe solid was dried on the vacuum

Sources & evidence

ORD record
ord-55b25909ccc740d9bfcccb23b84fbbf1
Source dataset
uspto-grants-2012_04
Patent number
US08163743B2

Reaction notes

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