Hydrochloric Acid → methyl-4-((6-(2-(dimethylamino)-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-yl)amino)benzoate

HRID 1894758ノート

反応式

HRID 1894758 の反応式
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH:11]([N:18]3[CH:22]=[CH:21][N:20]=[CH:19]3)[CH:12]([N:15]([CH3:17])[CH3:16])[CH2:13][CH3:14])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:23][O:24][C:25](=[O:33])[C:26]1[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=1.Cl>ClCCCl.CCCCO>[CH3:23][O:24][C:25](=[O:33])[C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:2]2[S:3][C:4]3[CH:10]=[C:9]([CH:11]([N:18]4[CH:22]=[CH:21][N:20]=[CH:19]4)[CH:12]([N:15]([CH3:17])[CH3:16])[CH2:13][CH3:14])[CH:8]=[CH:7][C:5]=3[N:6]=2)=[CH:28][CH:27]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 12082Methyl 4-aminobenzoateHCID 547620851-(2-bromobenzo[d]thiazol-6-yl)-1-(1H-imidazol-1-yl)-N,N-dimethylbutan-2-amine

生成物 1

HCID 54760075methyl-4-((6-(2-(dimethylamino)-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-yl)amino)benzoate

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 2631-Butanol溶媒

実験手順

A solution of 1-(2-bromobenzo[d]thiazol-6-yl)-1-(1H-imidazol-1-yl)-N,N-dimethyl-butan-2-amine (30 mg, 0.079 mmol), methyl-4-aminobenzoate (24 mg, 0.16 mmol) in 300 μL DCE and 300 μL n-BuOH was treated with 4N HCl (40 μL, 0.16 mmol) and refluxed overnight. The mixture was then partitioned between DCM and saturated NaHCO3 and the aqueous phase was extracted with DCM. The combined organic extracts were dried over Na2SO4, decanted and concentrated in vacuo. The residue was purified by PTLC using two 1 mm silica plates eluting with 5% MeOH (2N NH3)/DCM to provide methyl-4-((6-(2-(dimethylamino)-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-yl)amino)benzoate. MS (ESI+) m/z 450.19 [M+H]

後処理

  1. temperaturerefluxed overnight
  2. customThe mixture was then partitioned between DCM and saturated NaHCO3
  3. extractionthe aqueous phase was extracted with DCM
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. customdecanted
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by PTLC
  8. washeluting with 5% MeOH (2N NH3)/DCM

出典と根拠

ORDレコード
ord-192d47d735f543d7aa4f7c1affa89bd9
出典データセット
uspto-grants-2013_08
特許番号
US08513291B2

反応ノート

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