Imidazole → N-Methyl-2-(6-methylaminopyridin-3-yl)benzothiazol-6-amine

HRID 1851791Notes

Reaction equation

HRID 1851791 reaction equation
N[C:2]1[S:3][C:4]2[CH:10]=[C:9](O)[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:12][C:13]([Si](Cl)(C)C)([CH3:15])C.[NH:20]1[CH:24]=[CH:23][N:22]=[CH:21]1.[CH3:25][N:26](C=O)C>>[CH3:25][NH:26][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([C:12]3[CH:23]=[N:22][C:21]([NH:20][CH3:24])=[CH:15][CH:13]=3)[S:3][C:4]=2[CH:10]=1

Participants

5

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 334622-Amino-6-benzothiazolol

Product 1

HCID 24804556N-Methyl-2-(6-methylaminopyridin-3-yl)benzothiazol-6-amine

Procedure

A solution of 2-amino-6-hydroxybenzothiazole (5.00 g, 30.1 mmol), TBDMSCl (5.40 g, 1.2 equiv) and imidazole (2.46 g, 1.2 equiv) in DMF (160 ml) was stirred at ambient temperature for 16 h. The reaction mixture was then partitioned between water and ethyl acetate. The aqueous phase was extracted twice with ethyl acetate and the combined organics dried (MgSO4) and concentrated in vacuo. The crude product thus obtained was purified by silica gel chromatography by gradient elution (n-heptane:ethyl acetate) to yield 3.0 g of the title compound as a yellowish solid. 1H NMR δ 7.23 (br s, 2H) 7.18 (d, 1H) 7.16 (d, 1H) 6.70 (dd, 1H) 0.95 (s, 9H) 0.16 (s, 6 H); MS m/z (M+H) 281.

Workup

  1. customThe reaction mixture was then partitioned between water and ethyl acetate
  2. extractionThe aqueous phase was extracted twice with ethyl acetate
  3. dry with materialthe combined organics dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude product thus obtained
  6. customwas purified by silica gel chromatography by gradient elution (n-heptane:ethyl acetate)

Sources & evidence

ORD record
ord-f1744473e3984aa49fa21da7790efa57
Source dataset
uspto-grants-2015_02
Patent number
US08957215B2

Reaction notes

Loading…