1,2-Dichloroethane → HCID 86619629, compound

HRID 2265882Notes

Reaction equation

HRID 2265882 reaction equation
C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[F:15][C:16]1[CH:53]=[CH:52][C:19]([O:20][C:21]2[CH:26]=[CH:25][C:24]([S:27]([N:30]3[CH2:39][CH2:38][C:37]4[C:32](=[CH:33][CH:34]=[C:35]([O:40][CH2:41][CH2:42][N:43]5[CH2:48][CH2:47][O:46][CH2:45][CH2:44]5)[CH:36]=4)[CH:31]3[C:49](O)=[O:50])(=[O:29])=[O:28])=[CH:23][CH:22]=2)=[CH:18][CH:17]=1.[O:54]1[CH2:59][CH2:58][CH2:57][CH2:56][CH:55]1[O:60][NH2:61]>CN(C=O)C>[O:54]1[CH2:59][CH2:58][CH2:57][CH2:56][CH:55]1[O:60][NH:61][C:49]([CH:31]1[C:32]2[C:37](=[CH:36][C:35]([O:40][CH2:41][CH2:42][N:43]3[CH2:44][CH2:45][O:46][CH2:47][CH2:48]3)=[CH:34][CH:33]=2)[CH2:38][CH2:39][N:30]1[S:27]([C:24]1[CH:25]=[CH:26][C:21]([O:20][C:19]2[CH:18]=[CH:17][C:16]([F:15])=[CH:53][CH:52]=2)=[CH:22][CH:23]=1)(=[O:28])=[O:29])=[O:50]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 66879432HCID 66879432, compound

Product 1

HCID 86619629HCID 86619629, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 40 mg (0.264 mmol) of HOBt and 51 mg (0.264 mmol) of EDC in 2 ml of DMF was added dropwise to a solution of 98 mg (0.176 mmol) of 2-[4-(4-fluoro-phenoxy)benzenesulfonyl]-6-(2-morpholin-4-ylethoxy)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid and 46 mg (0.325 mmol) of O-(tetrahydropyran-2-yl)hydroxylamine in 3 ml of DMF at 0° C., and the mixture was stirred at room temperature. After standing overnight, it was poured onto H2O and extracted with ethyl acetate. The organic phase was dried with MgSO4 and concentrated. The residue was chromatographed on silica gel (dichloromethane→dichloromethane/methanol 99:1), the title compound being isolated as a colorless solid. Yield: 80%.

Workup

  1. additionit was poured onto H2O
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried with MgSO4
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel (dichloromethane→dichloromethane/methanol 99:1)

Sources & evidence

ORD record
ord-5f8f62975af7437f9e82c9dcc9253875
Source dataset
uspto-grants-2010_12
Patent number
US07858619B2

Reaction notes

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