Boron tribromide → N-ethyl-2-(ethylcarbamoylamino)-5-hydroxy-1,3-benzothiazole-7-carboxamide

HRID 712282Notes

Reaction equation

HRID 712282 reaction equation
B(Br)(Br)Br.[CH2:5]([NH:7][C:8]([C:10]1[C:18]2[S:17][C:16]([NH:19][C:20](=[O:24])[NH:21][CH2:22][CH3:23])=[N:15][C:14]=2[CH:13]=[C:12]([O:25]C)[CH:11]=1)=[O:9])[CH3:6]>C(Cl)Cl.CCOC(C)=O>[CH2:5]([NH:7][C:8]([C:10]1[C:18]2[S:17][C:16]([NH:19][C:20](=[O:24])[NH:21][CH2:22][CH3:23])=[N:15][C:14]=2[CH:13]=[C:12]([OH:25])[CH:11]=1)=[O:9])[CH3:6]

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 86663994N-ethyl-2-(ethylcarbamoylamino)-5-methoxy-1,3-benzothiazole-7-carboxamide

Product 1

HCID 86663995N-ethyl-2-(ethylcarbamoylamino)-5-hydroxy-1,3-benzothiazole-7-carboxamideYield 31%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Boron tribromide (8.72 mL, 8.72 mmol, 4M solution in DCM was added to a suspension of N-ethyl-2-(ethylcarbamoylamino)-5-methoxy-1,3-benzothiazole-7-carboxamide in dichloromethane (10 mL). The reaction was stirred at ambient temperature overnight then diluted with EtOAc, washed with saturated aqueous sodium hydrogen carbonate and brine and the organic layer dried (MgSO4), filtered and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel using DCM:MeOH 95:5. The product was obtained as a white solid, 212 mg, 31% yield.

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate and brine
  2. dry with materialthe organic layer dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by flash chromatography on silica gel
  6. customThe product was obtained as a white solid, 212 mg, 31% yield

Sources & evidence

ORD record
ord-ff4aa71a21dc4d7b96b4093ad8a8712d
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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