N-(5-methyl-7-oxo-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)acetamide → [5-(2-Acetylamino-5-methyl-7-oxo-4,5,6,7-tetrahydro-benzothiazole-6-carbonyl)-pyridin-2-yl]-methyl-carbamic acid tert-butyl ester

HRID 595090Notes

Reaction equation

HRID 595090 reaction equation
[C:1]([O:5][C:6](=[O:18])[N:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15](Cl)=[O:16])=[CH:11][N:10]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH3:19][CH:20]1[CH2:32][C:24]2[N:25]=[C:26]([NH:28][C:29](=[O:31])[CH3:30])[S:27][C:23]=2[C:22](=[O:33])[CH2:21]1>>[C:1]([O:5][C:6](=[O:18])[N:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH:21]2[CH:20]([CH3:19])[CH2:32][C:24]3[N:25]=[C:26]([NH:28][C:29](=[O:31])[CH3:30])[S:27][C:23]=3[C:22]2=[O:33])=[O:16])=[CH:11][N:10]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 4644134N-(5-methyl-7-oxo-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)acetamideHCID 86664608(5-Chlorocarbonyl-pyridin-2-yl)-methyl-carbamic acid tert-butyl ester

Product 1

HCID 86664607[5-(2-Acetylamino-5-methyl-7-oxo-4,5,6,7-tetrahydro-benzothiazole-6-carbonyl)-pyridin-2-yl]-methyl-carbamic acid tert-butyl ester

Procedure

A-13 is prepared via general procedure A1 starting from (5-chlorocarbonyl-pyridin-2-yl)-methyl-carbamic acid tert-butyl ester (A-10) (7.24 g, 26.8 mmol) and N-(5-methyl-7-oxo-4,5,6,7-tetrahydro-benzothiazol-2-yl)-acetamide (A-06) (5.00 g, 22.3 mmol). After evaporation of the solvent 7.72 g of A-13 is obtained that is used without further purification in the next step.

Workup

  1. customA-13 is prepared via general procedure A1
  2. customAfter evaporation of the solvent 7.72 g of A-13
  3. customis obtained
  4. customthat is used without further purification in the next step

Sources & evidence

ORD record
ord-99a2bec117a64494ac4276fc90d10102
Source dataset
uspto-grants-2016_01
Patent number
US09243000B2

Reaction notes

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