Hydrogen Bromide → HCID 86607627, compound

HRID 1990798Notes

Reaction equation

HRID 1990798 reaction equation
C(OC([N:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13]2[S:14][C:15]3[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:16]=3[N:17]=2)[CH2:8][CH2:7]1)=O)C.[BrH:23]>O>[BrH:23].[BrH:23].[Cl:22][C:20]1[CH:19]=[CH:18][C:16]2[N:17]=[C:13]([NH:12][CH:9]3[CH2:8][CH2:7][NH:6][CH2:11][CH2:10]3)[S:14][C:15]=2[CH:21]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 86607626HCID 86607626, compound

Product 1

HCID 86607627HCID 86607627, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4-(6-chloro-benzothiazol-2-ylamino)-piperidine-1-carboxylic acid ethyl ester (2.60 g, 7.65 mmol) in hydrobromic acid 48% in water (60 mL) was heated to reflux for 18 h. Removal of hydrobromic acid under reduced pressure and precipitation from ethanol (50 mL) provided 3.26 g (99%) of the title compound which was used directly in the next step. 1H NMR (400 MHz, DMSO): δ 1.69-1.79 (m, 2H), 2.14-2.17 (m, 2H), 3.01-3.09 (m, 2H), 3.32-3.35 (m, 2H), 4.06 (br s, 1H), 7.31 (dd, J=8.4 Hz, J=2.4 Hz, 1H), 7.42 (d, J=8.4 Hz, 1H), 7.88 (d, J=2.4 Hz, 1H), 8.52 (br s, 1H), 8.62 (br s, 1H), 9.00 (br s, 1H). MS (ISP): 266.0 [M−H]−.

Workup

  1. temperatureto reflux for 18 h
  2. customRemoval of hydrobromic acid
  3. customunder reduced pressure and precipitation from ethanol (50 mL)

Sources & evidence

ORD record
ord-61d2c111e0c24d3984cd4fd9bbf35a1d
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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