Triethylamine → 4-[(4-Methoxy-7-morpholin-4-yl-benzothiazole-2-carbonyl)-amino]-5-oxo-azepane-1-carboxylic acid tert-butyl ester

HRID 1244358Notes

Reaction equation

HRID 1244358 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH:12]([NH:15][C:16]([C:18]2[S:19][C:20]3[C:26]([N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)=[CH:25][CH:24]=[C:23]([O:33][CH3:34])[C:21]=3[N:22]=2)=[O:17])[CH:11]([OH:35])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C>CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11](=[O:35])[CH:12]([NH:15][C:16]([C:18]2[S:19][C:20]3[C:26]([N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)=[CH:25][CH:24]=[C:23]([O:33][CH3:34])[C:21]=3[N:22]=2)=[O:17])[CH2:13][CH2:14]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 691841154-Hydroxy-5-[(4-methoxy-7-morpholin-4-yl-benzothiazole-2-carbonyl)-amino]-azepane-1-carboxylic acid tert-butyl ester

Product 1

HCID 691841504-[(4-Methoxy-7-morpholin-4-yl-benzothiazole-2-carbonyl)-amino]-5-oxo-azepane-1-carboxylic acid tert-butyl esterYield 87.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of 0.56 g 4-hydroxy-5-[(4-methoxy-7-morpholin-4-yl-benzothiazole-2-carbonyl)-amino]-azepane-1-carboxylic acid tert-butyl ester in 10 ml dimethylsulfoxide were added 0.93 ml triethylamine, 10 ml dichlotomethane and a solution of 0.58 g sulfur trioxide pyridine complex in 8 ml dimethylsulfoxide. The mixture was stirred for 18 hours at room temperature. Extraction with water/ ethylacetate and chromatography on silicagel with dichloromethane/methanol 97:3 yielded 0.49 g (87%) 4-[(4-methoxy-7-morpholin-4-yl-benzothiazole-2-carbonyl)-amino]-5-oxo-azepane-1-carboxylic acid tert-butyl ester as yellow solid; M.p.: 95–97° C.; MS (ISP): m/e=505 (M+H+).

Workup

  1. extractionExtraction with water/ ethylacetate and chromatography on silicagel with dichloromethane/methanol 97:3

Sources & evidence

ORD record
ord-1744059e23b647b5a0f4ffe5903c58a7
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

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