Boron tribromide → HCID 86618574, compound

HRID 1922287Notes

Reaction equation

HRID 1922287 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-1bbd328b89ce459a93c5c898a918ac02
Source dataset
uspto-grants-2012_05
Patent number
US08173689B2

Reaction notes

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