Stannous Chloride → HCID 178448264, compound

HRID 1879635Notes

Reaction equation

HRID 1879635 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH3:9])=[CH:4][C:3]=1[C:10](=O)[CH:11]([C@@H:19]([C:23]1[CH:36]=[CH:35][C:26]([C:27]([NH:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[O:28])=[CH:25][CH:24]=1)[CH2:20][CH2:21][CH3:22])[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1.[N:38]([O-])=O.[Na+].Cl[Sn]Cl>Cl.O>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([C@H:11]([C:10]2[C:3]3[C:2](=[C:7]([F:8])[CH:6]=[C:5]([CH3:9])[CH:4]=3)[NH:1][N:38]=2)[C@@H:19]([C:23]2[CH:24]=[CH:25][C:26]([C:27]([NH:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[O:28])=[CH:35][CH:36]=2)[CH2:20][CH2:21][CH3:22])=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 24479Stannous ChlorideHCID 23668193Sodium NitriteHCID 58349463HCID 58349463, compound

Product 1

HCID 178448264HCID 178448264, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

The product from Step A (74 mg, 0.14 mmol) was suspended in concentrated HCl (1 mL) then cooled to 0° C. To the stirred suspension was added a solution of NaNO2 (7.5 mg, 0.11 mmol) in water, then the mixture was stirred for 30 minutes. Solid SnCl2 (47 mg, 0.25 mmol) was added, then the mixture was stirred for another 30 minutes. Ice was added, then the mixture was extracted with EtOAc. The organic phase was washed with water then saturated NaCl(aq), dried over Na2SO4, filtered, then concentrated. The residue was purified by reverse phase HPLC eluting with 10-70% acetonitrile/water+0.1% TFA. Following lyophilization, this afforded the title compound as a white solid. 1H NMR (500 MHz, CDCl3): δ 7.51 (d, J=7.9 Hz, 2H); 7.43 (d, J=8.1 Hz, 2H); 7.31 (d, J=8.2 Hz, 2H); 7.26 obs, 2H); 7.17 (s, 1H); 6.85-6.78 (m, 2H); 4.60 (d, J=11.6 Hz, 1H); 3.76-3.62 (m, 3H); 2.70 (t, J=5.6 Hz, 2H); 2.41 (s, 3H); 1.59-1.43 (m, 2H); 1.07-0.96 (m, 2H); 0.73 (t, J=7.3 Hz, 3H). LC1 2.36 min. (M+H)+ 522.

Workup

  1. stirringthe mixture was stirred for another 30 minutes
  2. additionIce was added
  3. extractionthe mixture was extracted with EtOAc
  4. washThe organic phase was washed with water
  5. dry with materialsaturated NaCl(aq), dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by reverse phase HPLC
  9. washeluting with 10-70% acetonitrile/water+0.1% TFA

Sources & evidence

ORD record
ord-27174d497ea348f5bf77ed5bfcbe6130
Source dataset
uspto-grants-2012_11
Patent number
US08318667B2

Reaction notes

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