1,2-Dichloroethane → HCID 58790352, compound

HRID 418601Notes

Reaction equation

HRID 418601 reaction equation
[O:1]=[C:2]([NH:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)[CH2:3][C:4]([OH:6])=O.C1C=CC2N(O)N=NC=2C=1.[F:24][C:25]1[CH:26]=[C:27]([NH2:47])[CH:28]=[CH:29][C:30]=1[O:31][C:32]1[CH:37]=[CH:36][N:35]=[C:34]2[CH:38]=[C:39]([C:41]3[N:42]([CH3:46])[CH:43]=[CH:44][N:45]=3)[S:40][C:33]=12.C(Cl)CCl.C([O-])(O)=O.[Na+]>CN(C=O)C>[F:24][C:25]1[CH:26]=[C:27]([NH:47][C:4](=[O:6])[CH2:3][C:2]([NH:7][C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[O:1])[CH:28]=[CH:29][C:30]=1[O:31][C:32]1[CH:37]=[CH:36][N:35]=[C:34]2[CH:38]=[C:39]([C:41]3[N:42]([CH3:46])[CH:43]=[CH:44][N:45]=3)[S:40][C:33]=12

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 219394713-Oxo-3-[(pyridin-3-yl)amino]propanoic acidHCID 594244803-Fluoro-4-(2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yloxy)benzenamine

Product 1

HCID 58790352HCID 58790352, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the acid 39 (58 mg, 0.32 mmol) and HOBt (47 mg, 0.35 mmol) in DMF (5 mL), was added amine 9 (108 mg, 0.32 mmol). After stirring for 5 min, EDC (75 mg, 0.39 mmol) was added and the reaction mixture was stirred overnight at room temperature then poured into dilute NaHCO3 solution and extracted with EtOAc. The extract was dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by preparative HPLC (Aquasil C-18, gradient: MeOH in water 60% to 95%) to afford the title compound 40 as a white solid. (20 mg, 12%) 1H NMR (DMSO-d6) δ (ppm): 10.65 (s, 1H), 10.50 (s, 1H), 8.73 (d, 1H), 8.50 (d, 1H), 8.26 (dd, 1H), 8.05 (m, 1H), 7.88 (s, 1H), 7.87 (dd, 1H), 7.48 (t, 1H), 7.41 (m, 2H), 7.35 (m, 1H), 6.69 (d, 1H), 3.99 (s, 3H), 3.56 (s, 2H). MS (m/z): 503.1 (M+H).

Workup

  1. stirringthe reaction mixture was stirred overnight at room temperature
  2. extractionextracted with EtOAc
  3. dry with materialThe extract was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by preparative HPLC (Aquasil C-18, gradient: MeOH in water 60% to 95%)

Sources & evidence

ORD record
ord-0dac295021f1406a86dc7b7032b7903d
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

Loading…