Ethyl Acetate → HCID 57826686, compound

HRID 1845696Notes

Reaction equation

HRID 1845696 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([C:12]([NH:14][C@@H:15]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=3)[CH2:16][N:17]3[C:25](=[O:26])[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:18]3=[O:27])=[O:13])[S:10][CH:11]=2)=[C:5]([CH3:36])[N:4]=[N:3]1.C1C(=O)N([Cl:44])C(=O)C1.CCOC(C)=O>CN(C)C=O>[Cl:44][C:11]1[S:10][C:9]([C:12]([NH:14][C@@H:15]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=2)[CH2:16][N:17]2[C:25](=[O:26])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]2=[O:27])=[O:13])=[CH:8][C:7]=1[C:6]1[N:2]([CH3:1])[N:3]=[N:4][C:5]=1[CH3:36]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 31398ChlorosuccinimideHCID 57826851HCID 57826851, compound

Product 1

HCID 57826686HCID 57826686, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-N-{(1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-[(3-fluorophenyl)methyl]ethyl}-2-thiophenecarboxamide (254 mg, 0.454 mmol), and NCS (60.6 mg, 0.454 mmol) in N,N-Dimethylformamide (DMF) (5 mL) to was heated at 40° C. overnight. The reaction mixture was taken into EtOAc, which was washed with H2O 3× and brine, dried (Na2SO4) and concentrated. The residue was purified on a 25 g Biotage column, which was eluted with 50-100% EtOAc/hexane to give 76 mg (28%) of product as a white foamy solid and 63 mg of recovered starting material. LC-MS (ES) m/z 538.0 (M+H)+.

Workup

  1. washwas washed with H2O 3× and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified on a 25 g Biotage column, which
  5. washwas eluted with 50-100% EtOAc/hexane

Sources & evidence

ORD record
ord-083a739ec66746f78040d8e06bf57a92
Source dataset
uspto-grants-2015_02
Patent number
US08946278B2

Reaction notes

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