Stannous chloride dihydrate → HCID 59625705, compound

HRID 409929Notes

Reaction equation

HRID 409929 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=2[N+:19]([O-])=O)=[CH:4][CH:3]=1.O.O.Cl[Sn]Cl.C([O-])(O)=O.[Na+]>CCO>[NH2:19][C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][C:9]=1[NH:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[C:13]([O:15][CH3:16])=[O:14]

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 59625834HCID 59625834, compound

Product 1

HCID 59625705HCID 59625705, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 27c (1.4 g, 4.8 mmol) and SnCl2.2H2O (4.9 g, 21.7 mmol) in EtOH (50 mL) was stirred at 80° C. After 4 h, the mixture was cooled to room temperature and was slowly added to saturated aqueous NaHCO3. The solid was filtered and washed with H2O. The solid was triturated with EtOAc and the filtrate was concentrated. The crude product 27d was used in the next reaction without purification. MS m/z (M+H+) 261.1.

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. filtrationThe solid was filtered
  3. washwashed with H2O
  4. customThe solid was triturated with EtOAc
  5. concentrationthe filtrate was concentrated
  6. customThe crude product 27d was used in the next reaction without purification

Sources & evidence

ORD record
ord-e010f44bec014e43803a1e91883bbfbf
Source dataset
uspto-grants-2014_06
Patent number
US08759533B2

Reaction notes

Loading…