6-Aminobenzothiazole → (2E)-N-Benzothiazol-6-yl-3-[6-(tert-butyl)-2-methyl(3-pyridyl)]prop-2-enamide

HRID 730280Notes

Reaction equation

HRID 730280 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([CH3:11])[C:8](/[CH:12]=[CH:13]/[C:14]([OH:16])=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:17][C:18]1[CH:26]=[CH:25][C:21]2[N:22]=[CH:23][S:24][C:20]=2[CH:19]=1>>[S:24]1[C:20]2[CH:19]=[C:18]([NH:17][C:14](=[O:16])/[CH:13]=[CH:12]/[C:8]3[C:9]([CH3:11])=[N:10][C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:6][CH:7]=3)[CH:26]=[CH:25][C:21]=2[N:22]=[CH:23]1

Participants

3

Reactant 2

HCID 682886-AminobenzothiazoleHCID 57808155(2E)-3-[6-(1,1-Dimethylethyl)-2-methyl-3-pyridinyl]-2-propenoic acid

Product 1

HCID 10126040(2E)-N-Benzothiazol-6-yl-3-[6-(tert-butyl)-2-methyl(3-pyridyl)]prop-2-enamide

Procedure

Analogous to the procedure used to prepare Example 1, (2E)-3-[6-(tert-butyl)-2-methyl(3-pyridyl)]prop-2-enoic acid, Example 75(c), (220 mg, 1.0 mmol) and 6-aminobenzothiazole (150 mg, 1.0 mmol, Lancaster) provided, after purification by silica gel chromatography (55:45 hexane:EtOAc), the title compound as a pale yellow amorphous solid. MS (ESI, pos. ion) m/z: 352 (M+1).

Workup

  1. customprovided
  2. customafter purification by silica gel chromatography (55:45 hexane:EtOAc)

Sources & evidence

ORD record
ord-132a1aea1abc41e0adac1d02a8a93b80
Source dataset
uspto-grants-2009_09
Patent number
US07582657B2

Reaction notes

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