Dichloromethane → (E)-N-(Tetrahydro-pyran-2-yloxy)-3-(1-{4-[1-(2-morpholin-4-yl-ethyl)-1H-[1,2,3]triazol-4-yl]-benzenesulfonyl}-1H-pyrrol-3-yl)-acrylamide

HRID 2408452Notes

Reaction equation

HRID 2408452 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][N:9]=[N+:10]=[N-:11])[CH2:3][CH2:2]1.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].[C:25]([C:27]1[CH:32]=[CH:31][C:30]([S:33]([N:36]2[CH:40]=[CH:39][C:38](/[CH:41]=[CH:42]/[C:43]([NH:45][O:46][CH:47]3[CH2:52][CH2:51][CH2:50][CH2:49][O:48]3)=[O:44])=[CH:37]2)(=[O:35])=[O:34])=[CH:29][CH:28]=1)#[CH:26].C(Cl)Cl>O.CC(O)(C)C>[O:48]1[CH2:49][CH2:50][CH2:51][CH2:52][CH:47]1[O:46][NH:45][C:43](=[O:44])/[CH:42]=[CH:41]/[C:38]1[CH:39]=[CH:40][N:36]([S:33]([C:30]2[CH:29]=[CH:28][C:27]([C:25]3[N:11]=[N:10][N:9]([CH2:8][CH2:7][N:4]4[CH2:5][CH2:6][O:1][CH2:2][CH2:3]4)[CH:26]=3)=[CH:32][CH:31]=2)(=[O:35])=[O:34])[CH:37]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 27370154-(2-Azidoethyl)morpholineHCID 23667548Sodium AscorbateHCID 86621705(E)-3-[1-(4-Ethynyl-benzenesulfonyl)-1H-pyrrol-3-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide

Product 1

HCID 86621706(E)-N-(Tetrahydro-pyran-2-yloxy)-3-(1-{4-[1-(2-morpholin-4-yl-ethyl)-1H-[1,2,3]triazol-4-yl]-benzenesulfonyl}-1H-pyrrol-3-yl)-acrylamideYield 27%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a stirred mixture of 2-morpholino-ethylazide (0.30 mmol) in water (2 ml) are added CuSO4 pentahydrate (0.02 mmol), sodiumascorbate (0.04 mmol) and (E)-3-[1-(4-Ethynyl-benzenesulfonyl)-1H-pyrrol-3-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide (0.30 mmol) in t-BuOH (1 ml) at room temperature. The reaction mixture is stirred over night. After addition of DCM the organic phase is separated, evaporated under reduced pressure and purified by prep. HPLC yielding 0.081 mmol of the title compound.

Workup

  1. customis separated
  2. customevaporated under reduced pressure
  3. custompurified by prep

Sources & evidence

ORD record
ord-28b56c5e5b10477ba0213205ec36061e
Source dataset
uspto-grants-2014_08
Patent number
US08815855B2

Reaction notes

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