Hydrogen Bromide → HCID 178419253, compound

HRID 1382536Notes

Reaction equation

HRID 1382536 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:12]=[CH:11][C:10]2[N:9]([CH2:13][CH2:14][N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[N:8]=[C:7]3[C:20]4[CH:26]=[CH:25][C:24]([O:27]C)=[CH:23][C:21]=4[S:22][C:5]=1[C:6]=23.B(Br)(Br)[Br:30].CO.[BrH:35]>ClC(Cl)C>[BrH:30].[BrH:35].[NH2:3][C:4]1[CH:12]=[CH:11][C:10]2[N:9]([CH2:13][CH2:14][N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[N:8]=[C:7]3[C:20]4[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][C:21]=4[S:22][C:5]=1[C:6]=23

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 887MethanolHCID 25134Boron tribromideHCID 14406787HCID 14406787, compound

Product 1

HCID 178419253HCID 178419253, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
78 °C

Procedure

A 25° C. suspension of 75 g (0:17 mol) of 5-amino-N,N-diethyl-8-methoxy-2H-[1]benzothiopyrano[4,3,2-cd]indazole-2-ethanamine, dihydrochloride (1) in 1.35 L of dichloroethane was treated dropwise with 213 g (0.85 mol) of boron tribromide. The mixture was heated at 78° C. for 16 hr, treated cautiously with 1.5 L of methanol, then heated at reflux for 6 hr. After cooling to 25° C., then chilling at -5° C. overnight, the precipitated solids were collected by filtration, washed with cold methanol, and dried at 2 mm/48° C./24 hr to give 84.3 g (96%) of 7 as a salt with 2.0 equivalents of hydrogen bromide, mp 318° C. (dec), 98.3% pure by HPLC.

Workup

  1. temperatureheated
  2. temperatureat reflux for 6 hr
  3. temperatureAfter cooling to 25° C.
  4. temperaturechilling at -5° C. overnight
  5. filtrationthe precipitated solids were collected by filtration
  6. washwashed with cold methanol
  7. customdried at 2 mm/48° C./24 hr

Sources & evidence

ORD record
ord-1f59da52867a419a9bdc9218dca0981f
Source dataset
uspto-grants-1989_02
Patent number
US04806654

Reaction notes

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