1,2-Dichloroethane → HCID 86708255, compound

HRID 534206Notes

Reaction equation

HRID 534206 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]([N:5]([CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:23]2[CH:31]=[CH:30][C:26]([C:27]([OH:29])=O)=[CH:25][CH:24]=2)[CH2:18][CH2:17]1)[C@@H:6]1[CH2:8][C@H:7]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:4].[CH3:34][S:35]([NH2:38])(=[O:37])=[O:36].C(Cl)CCl>CN(C)C=O.CN(C1C=CN=CC=1)C>[CH3:34][S:35]([NH:38][C:27](=[O:29])[C:26]1[CH:25]=[CH:24][C:23]([CH2:22][N:19]2[CH2:18][CH2:17][CH:16]([CH2:15][N:5]([C@@H:6]3[CH2:8][C@H:7]3[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:3](=[O:4])[C:2]([F:32])([F:1])[F:33])[CH2:21][CH2:20]2)=[CH:31][CH:30]=1)(=[O:37])=[O:36]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 72879MethanesulfonamideHCID 86708253HCID 86708253, compound

Product 1

HCID 86708255HCID 86708255, compoundYield 46.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-((4-((2,2,2-trifluoro-N-(trans-2-phenylcyclopropyl)acetamido)methyl)piperidin-1-yl)methyl)benzoic acid (150 mg, 0.326 mmol) in N,N-dimethylformamide (DMF) (2 mL) were added methanesulfonamide (37.2 mg, 0.391 mmol), EDC (74.9 mg, 0.391 mmol) and DMAP (39.8 mg, 0.326 mmol), and the mixture was stirred at room temperature for 18 h. The reaction was quenched with 10% NH4Cl aqueous solution and extracted with EtOAc(3×). The extract was dried (Na2SO4) and concentrated. The residue was purified using column chromatography (silica gel, 0 to 100% EtOAc/hexaens) to give 82 mg of product as off-white solid. MS: (M+H)+=538.3. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.38-1.74 (m, 4H), 1.91-2.22 (m, 3H), 2.47 (m, 1H), 2.98-3.11 (m, 2H), 3.21 (d, J=6.82 Hz, 1H), 3.37-3.66 (m, 7H), 4.39 (s, 2H), 7.04-7.38 (m, 5H), 7.67 (d, J=8.34 Hz, 2H), 8.03 (d, J=8.08 Hz, 2H).

Workup

  1. customThe reaction was quenched with 10% NH4Cl aqueous solution
  2. extractionextracted with EtOAc(3×)
  3. dry with materialThe extract was dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified

Sources & evidence

ORD record
ord-03ff613f3191476cb19169c339011177
Source dataset
uspto-grants-2014_10
Patent number
US08853408B2

Reaction notes

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