4-Nitrophenyl benzo[d]thiazol-2-ylcarbamate → ethyl 2-(4-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-(methyl(2-phenoxyethyl)amino)thiazole-4-carboxylate

HRID 2178222Notes

Reaction equation

HRID 2178222 reaction equation
[O:1]1[CH2:6][CH2:5][NH:4][C:3]2[CH:7]=[C:8]([C:11]3[S:12][C:13]([N:21]([CH3:31])[CH2:22][CH2:23][O:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:15]=3)[CH:9]=[CH:10][C:2]1=2.[S:32]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[N:34]=[C:33]1[NH:41][C:42](=O)[O:43]C1C=CC([N+]([O-])=O)=CC=1>C(#N)C>[S:32]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[N:34]=[C:33]1[NH:41][C:42]([N:4]1[CH2:5][CH2:6][O:1][C:2]2[CH:10]=[CH:9][C:8]([C:11]3[S:12][C:13]([N:21]([CH3:31])[CH2:22][CH2:23][O:24][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:15]=3)=[CH:7][C:3]1=2)=[O:43]

Participants

4

Reactant 2

HCID 594186764-Nitrophenyl benzo[d]thiazol-2-ylcarbamateHCID 59418724ethyl 2-(3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-(methyl(2-phenoxyethyl)amino)thiazole-4-carboxylate

Product 1

HCID 59418665ethyl 2-(4-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-(methyl(2-phenoxyethyl)amino)thiazole-4-carboxylateYield 310.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

To ethyl 2-(3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-(methyl(2-phenoxyethyl)amino)thiazole-4-carboxylate (20B) (0.150 g, 0.34 mmol) and 4-nitrophenyl benzo[d]thiazol-2-ylcarbamate (19) (0.349 g, 0.11 mmol) was added acetonitrile (10 mL). The reaction mixture was allowed to heat to 85° C. and stirred for 8 hours. Then the reaction mixture was allowed to heat at 70° C. and stirred overnight. The reaction mixture was allowed to cool to rt and concentrated under reduced pressure. To the concentrate was added EtOAc and water and filtered. The layers of the filtrate were separated and extracted with EtOAc. The combined organic extracts were washed sequentially with water, brine, dried over MgSO4, filtered, and concentrated under reduced pressure to provide 0.21 g (quantitative) ethyl 2-(4-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-(methyl(2-phenoxyethyl)amino)thiazole-4-carboxylate (20C): LC/MS (APCI): m/z 616.3 (M+H).

Workup

  1. temperatureto heat at 70° C.
  2. stirringstirred overnight
  3. temperatureto cool to rt
  4. concentrationconcentrated under reduced pressure
  5. additionTo the concentrate was added EtOAc and water
  6. filtrationfiltered
  7. customThe layers of the filtrate were separated
  8. extractionextracted with EtOAc
  9. washThe combined organic extracts were washed sequentially with water, brine
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-18a52da9ff534ff18c4e8270615449a9
Source dataset
uspto-grants-2015_06
Patent number
US09067928B2

Reaction notes

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