Triethylamine → N-(2-tetrahydropyranyloxy)-2-[4-cyclopropylaminocarbonyl-7-(5-(4-(5-oxazolyl)phenyl)-2-thienyl)-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetamide

HRID 1063925Notes

Reaction equation

HRID 1063925 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9](=[O:36])[CH2:10][C:11]1([C:20]2[S:21][C:22]([C:25]3[CH:30]=[CH:29][C:28]([C:31]4[O:35][CH:34]=[N:33][CH:32]=4)=[CH:27][CH:26]=3)=[CH:23][CH:24]=2)[S:17](=[O:19])(=[O:18])[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.C(N(CC)CC)C.[CH:44]1([NH:47][C:48](OC2C=CC=CC=2)=[O:49])[CH2:46][CH2:45]1.C(OCC)(=O)C>CN(C)C=O>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9](=[O:36])[CH2:10][C:11]1([C:20]2[S:21][C:22]([C:25]3[CH:30]=[CH:29][C:28]([C:31]4[O:35][CH:34]=[N:33][CH:32]=4)=[CH:27][CH:26]=3)=[CH:23][CH:24]=2)[S:17](=[O:18])(=[O:19])[CH2:16][CH2:15][N:14]([C:48]([NH:47][CH:44]2[CH2:46][CH2:45]2)=[O:49])[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 13648483Phenyl cyclopropylcarbamateHCID 22276407N-(2-tetrahydropyranyloxy)-2-[7-(5-(4-(5-oxazolyl)phenyl)-2-thienyl)-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetamide

Product 1

HCID 22276946N-(2-tetrahydropyranyloxy)-2-[4-cyclopropylaminocarbonyl-7-(5-(4-(5-oxazolyl)phenyl)-2-thienyl)-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetamideYield 56.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of N-(2-tetrahydropyranyloxy)-2-[7-(5-(4-(5-oxazolyl)phenyl)-2-thienyl)-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetamide (100 mg) in N,N-dimethylformamide (3 ml) was added triethylamine (57 mg) and cyclopropylaminocarbonyloxybenzene (40 mg) and the reaction mixture was heated at 50° C. for 4 hours. The mixture was added ethyl acetate and the solution was washed with successively water, a 5% aqueous citric acid-solution, a satuated aqueous sodium hydrogencarbonate and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel 60 (2% methanol-chloroform) to give N-(2-tetrahydropyranyloxy)-2-[4-cyclopropylaminocarbonyl-7-(5-(4-(5-oxazolyl)phenyl)-2-thienyl)-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetamide (65 mg) as a pale yellow powder.

Workup

  1. washthe solution was washed with successively water
  2. dry with materiala 5% aqueous citric acid-solution, a satuated aqueous sodium hydrogencarbonate and brine, dried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on silica gel 60 (2% methanol-chloroform)

Sources & evidence

ORD record
ord-bee72f59be834b0b838c7bb4f0e572d3
Source dataset
uspto-grants-2005_11
Patent number
US06967197B2

Reaction notes

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