Boron tribromide → HCID 86618574, compound

HRID 2370579Notes

Reaction equation

HRID 2370579 reaction equation
[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][CH2:9][C@H:8]([NH:12][C:13]2[S:14][C:15]3[CH:21]=[C:20]([O:22]C)[CH:19]=[CH:18][C:16]=3[N:17]=2)[CH2:7]1)(=[O:5])=[O:4])[CH3:2].B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl.O.C(OCC)(=O)C>[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][CH2:9][C@H:8]([NH:12][C:13]2[S:14][C:15]3[CH:21]=[C:20]([OH:22])[CH:19]=[CH:18][C:16]=3[N:17]=2)[CH2:7]1)(=[O:4])=[O:5])[CH3:2]

Participants

7

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 86618572HCID 86618572, compound

Product 1

HCID 86618574HCID 86618574, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (S)—N-(1-(ethylsulfonyl)piperidin-3-yl)-6-methoxybenzo[d]thiazol-2-amine (1.22 g, 3.43 mmol) in dichloromethane (25 ml) under nitrogen atmosphere was treated with boron tribromide (1M in dichloromethane, 7.5 ml) at 0° C. Stirring was continued for 10 min at 0° C. and for ˜135 min at ambient temperature. The reaction mixture was carefully diluted with water (50 ml), ethyl acetate (200 ml) and treated with solid sodium bicarbonate (until no further gas development was observed). The mixture was stirred until phases became clear. The separated organic phase was washed with saturated sodium bicarbonate solution (2×75 ml), water (75 ml), brine (75 ml) and dried over sodium sulfate. Concentration in vacuo afforded crude (S)-2-(1-(ethylsulfonyl)piperidin-3-ylamino)benzo[d]thiazol-6-ol which was used in the next step without further purification. Yield: 1.15 g. ES/MS m/z 342.0 (MH+), Rt=1.86 min.

Workup

  1. stirringThe mixture was stirred until phases
  2. washThe separated organic phase was washed with saturated sodium bicarbonate solution (2×75 ml), water (75 ml), brine (75 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-c1506afcc1e8426582a708d19de53e6c
Source dataset
uspto-grants-2014_04
Patent number
US08710048B2

Reaction notes

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