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]-ethyl-carbamic acid tert-butyl ester

HRID 595091Notes

Reaction equation

HRID 595091 reaction equation
[C:1]([O:5][C:6](=[O:19])[N:7]([C:10]1[CH:15]=[CH:14][C:13]([C:16](Cl)=[O:17])=[CH:12][N:11]=1)[CH2:8][CH3:9])([CH3:4])([CH3:3])[CH3:2].[CH3:20][CH:21]1[CH2:33][C:25]2[N:26]=[C:27]([NH:29][C:30](=[O:32])[CH3:31])[S:28][C:24]=2[C:23](=[O:34])[CH2:22]1>>[C:1]([O:5][C:6](=[O:19])[N:7]([C:10]1[CH:15]=[CH:14][C:13]([C:16]([CH:22]2[CH:21]([CH3:20])[CH2:33][C:25]3[N:26]=[C:27]([NH:29][C:30](=[O:32])[CH3:31])[S:28][C:24]=3[C:23]2=[O:34])=[O:17])=[CH:12][N:11]=1)[CH2:8][CH3:9])([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 86664610(5-Chlorocarbonyl-pyridin-2-yl)-ethyl-carbamic acid tert-butyl ester

Product 1

HCID 86664609[5-(2-Acetylamino-5-methyl-7-oxo-4,5,6,7-tetrahydro-benzothiazole-6-carbonyl)-pyridin-2-yl]-ethyl-carbamic acid tert-butyl ester

Procedure

A-14 is prepared via general procedure A1 starting from (5-chlorocarbonyl-pyridin-2-yl)-ethyl-carbamic acid tert-butyl ester (A-09) (7.62 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 8.62 g of A-14 are obtained which is used without further purification in the next step.

Workup

  1. customA-14 is prepared via general procedure A1
  2. customAfter evaporation of the solvent 8.62 g of A-14
  3. customare obtained which
  4. customis used without further purification in the next step

Sources & evidence

ORD record
ord-04df64c44c4d4c779dbe73bf8b57c1e2
Source dataset
uspto-grants-2016_01
Patent number
US09243000B2

Reaction notes

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