Bromide ion → HCID 49712243, compound

HRID 1991224Notes

Reaction equation

HRID 1991224 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:5]=2[N:6]=1.[Br-].[NH:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[CH:14]1.[CH3:22][C:23](C)([O-:25])C.[K+]>>[N:13]1([CH2:22][C:23]([NH:11][C:8]2[CH:9]=[CH:10][C:4]3[S:3][C:2]([CH3:1])=[N:6][C:5]=3[CH:7]=2)=[O:25])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[CH:14]1

Participants

5

Reactant 4

HCID 259Bromide ionHCID 5798BenzimidazoleHCID 362295-Benzothiazolamine, 2-methyl-HCID 23665647Potassium tert-butoxide

Product 1

HCID 49712243HCID 49712243, compoundYield 6.2%

Procedure

2-Methyl-benzothiazol-5-ylamine (32 mg, 0.2 mmol) and bromoacethyl bromide were added to a suspension of (N,N-diisopropyl)aminomethylpolystyrene resin (170 mg) in anhydrous TBF (2 mL) and the reaction mixture was shaken for 4 h at ambient temperature. The resin was then filtered off. 1H-benzoimidazole (35 mg, 0.3 mmol) and potassium tert-butoxide (0.36 mL of 1 M solution in THF, 0.36 mmol,) were added and the mixture was stirred at 55° C. for 24 h. The crude product was purified on a preparative LC/MS (XTerra C8 column 19×100 mm, 0.1 M aqueous NH4Ac/CH3CN). The pooled to fractions were lyophilized to afford 4 mg (6%) of the title compound. Calculated for C17H14N4OS m/z: 322.39, found 323.0 [M+H]+.

Workup

  1. filtrationThe resin was then filtered off
  2. stirringthe mixture was stirred at 55° C. for 24 h
  3. customThe crude product was purified on a preparative LC/MS (XTerra C8 column 19×100 mm, 0.1 M aqueous NH4Ac/CH3CN)

Sources & evidence

ORD record
ord-d7585d2cd74348898fe6779f0d7b1ab8
Source dataset
uspto-grants-2010_01
Patent number
US07645784B2

Reaction notes

Loading…