1,2-Dichloroethane → HCID 178445684, compound

HRID 1992791Notes

Reaction equation

HRID 1992791 reaction equation
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12]([C:14]2[N:18]([CH2:19][C:20]3[CH:28]=[CH:27][C:23]([C:24]([OH:26])=O)=[CH:22][CH:21]=3)[N:17]=[C:16]([C:29]3[CH:34]=[C:33]([F:35])[C:32]([F:36])=[C:31]([F:37])[CH:30]=3)[CH:15]=2)=[O:13])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[NH2:57][C:58]1[NH:62][N:61]=[N:60][N:59]=1.C(Cl)CCl>CN(C=O)C.C(OCC)(=O)C>[C:1]([C@H:5]1[CH2:6][CH2:7][C@H:8]([NH:11][C:12]([C:14]2[N:18]([CH2:19][C:20]3[CH:28]=[CH:27][C:23]([C:24]([NH:57][C:58]4[NH:62][N:61]=[N:60][N:59]=4)=[O:26])=[CH:22][CH:21]=3)[N:17]=[C:16]([C:29]3[CH:34]=[C:33]([F:35])[C:32]([F:36])=[C:31]([F:37])[CH:30]=3)[CH:15]=2)=[O:13])[CH2:9][CH2:10]1)([CH3:3])([CH3:2])[CH3:4]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 178445686HCID 178445686, compoundHCID 178509299HCID 178509299, compound

Product 1

HCID 178445684HCID 178445684, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the intermediate from step F (90 mg, 0.175 mmol) in DMF was added HOAt (36 mg, 0.26 mmol), DIEA (92 μL, 0.52 mmol), amino tetrazole (45 mg, 0.52 mmol) and EDC (50 mg, 0.26 mmol). The reaction 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): 8.42 (d, J=8.0 Hz, 1H), 8.03 (d, J=8.2 Hz, 2H), 7.68 (dd, J=6.6, 8.7 Hz, 2H), 7.39 (s, 1H), 7.35 (d, J=8.3 Hz, 2H), 5.81 (s, 2H), 3.63 (m, 1H), 1.87 (d, J=10.9 Hz, 2H), 1.76 (d, J=11.7 Hz, 2H), 1.2-1.0 (m, 4H), 0.83 (s, 9H). LC-MS: 2.50 min; (M+H)=581.3.

Workup

  1. waitThe reaction 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-58fa4f3eac094273a6abf1e10013aa26
Source dataset
uspto-grants-2010_01
Patent number
US07649009B2

Reaction notes

Loading…