Hydrogen Bromide → HCID 178509116, compound

HRID 57281Notes

Reaction equation

HRID 57281 reaction equation
OS(O)(=O)=O.[BrH:6].[NH2:7][C:8]1[C:9]([C:17]2[S:18][C:19]3[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=3[N:21]=2)=[C:10]([CH2:13][CH2:14][CH2:15]O)[NH:11][N:12]=1.[OH-].[Na+]>>[S:18]1[C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=[C:17]1[C:9]1[C:10]([CH2:13][CH2:14][CH2:15][Br:6])=[N:11][NH:12][C:8]=1[NH2:7]

Participants

5

Reactant 4

HCID 260Hydrogen BromideHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 66768172HCID 66768172, compound

Product 1

HCID 178509116HCID 178509116, compoundYield 80%

Procedure

To a solution of concentrated H2SO4 (3 mL) and hydrobromic acid (6 mL of 48%) was added 3-(5-amino-4-benzothiazol-2-yl-2H-pyrazol-3-yl)-propan-1-ol (810 mg, 3.0 mmol). The resulting mixture was refluxed for 2 hrs. The mixture was cooled to room temperature, poured into ice water, and adjusted to pH 3-4 using 5% NaOH solution. The resulting sticky solid was isolated by filtration, washed with water and air-dried to yield 815 mg (80%) of 4-benzothiazol-2-yl-5-(3-bromopropyl)-2H-pyrazol-3-ylamine as a cream coloured solid. The crude material was used in the subsequent step without further purification. MS (m/z, ES+): 337.1 (Br79M+1, 61%), 339.1 (Br81M+1, 59%), 257.2 (M-HBr, 100%).

Workup

  1. temperatureThe resulting mixture was refluxed for 2 hrs
  2. customThe resulting sticky solid was isolated by filtration
  3. washwashed with water
  4. customair-dried

Sources & evidence

ORD record
ord-9e9453d281f540a7abc1c4a7de60857d
Source dataset
uspto-grants-2016_09
Patent number
US09434720B2

Reaction notes

Loading…