1,2-Dichloroethane → HCID 178522672, compound

HRID 1992795Notes

Reaction equation

HRID 1992795 reaction equation
[F:1][C:2]([F:38])([F:37])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[N:17]([CH2:18][C:19]3[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=3)[N:16]=[C:15]([C:28]3[CH:33]=[C:32]([F:34])[C:31]([F:35])=[C:30]([F:36])[CH:29]=3)[CH:14]=2)=[O:12])=[CH:6][CH:5]=1.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[NH2:58][C:59]1[NH:63][N:62]=[N:61][N:60]=1.C(Cl)CCl>CN(C=O)C.C(OCC)(=O)C>[NH:60]1[C:59]([NH:58][C:23]([C:22]2[CH:26]=[CH:27][C:19]([CH2:18][N:17]3[C:13]([C:11]([NH:10][C:7]4[CH:8]=[CH:9][C:4]([O:3][C:2]([F:38])([F:1])[F:37])=[CH:5][CH:6]=4)=[O:12])=[CH:14][C:15]([C:28]4[CH:33]=[C:32]([F:34])[C:31]([F:35])=[C:30]([F:36])[CH:29]=4)=[N:16]3)=[CH:20][CH:21]=2)=[O:24])=[N:63][N:62]=[N:61]1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 86614808HCID 86614808, compoundHCID 178509299HCID 178509299, compound

Product 1

HCID 178522672HCID 178522672, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the intermediate from step B (45 mg, 0.84 mmol) in DMF was added HOAt (17 mg, 0.126 mmol), DIEA (44 μL, 0.252 mmol), amino tetrazole (22 mg, 0.252 mmol) and EDC (24 mg, 0.126 mmol). The resulting solution was left stirring at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate (20 mL), and washed with 1N HCl. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified on the Gilson reverse phase HPLC to give the title compound. 1H NMR (DMSO, 500 MHz): 8.04 (d, J=8.3 Hz, 2H), 7.82 (d, J=9.2 Hz, 2H), 7.74 (dd, J=6.9, 8.7 Hz, 2H), 7.64 (s, 1H), 7.38 (d, J=7.9 Hz, 2H), 5.85 (s, 2H). LC-MS: 2.56 min; (M+H)=603.1.

Workup

  1. waitThe resulting solution was left
  2. washwashed with 1N HCl
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified on the Gilson reverse phase HPLC

Sources & evidence

ORD record
ord-142a146bd3f148aeaca510e7f451811b
Source dataset
uspto-grants-2010_01
Patent number
US07649009B2

Reaction notes

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