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

HRID 1698111Notes

Reaction equation

HRID 1698111 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 (Q-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, 6H); 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 (Q-heptane:ethyl acetate)

Sources & evidence

ORD record
ord-1f56b7fd2ad74233bff0a4622d4dced7
Source dataset
uspto-grants-2012_04
Patent number
US08163928B2

Reaction notes

Loading…