Stannous chloride dihydrate → HCID 59471998, compound

HRID 78620Notes

Reaction equation

HRID 78620 reaction equation
O.O.Cl[Sn]Cl.[NH2:6][C:7]1[N:8]=[CH:9][C:10]([C:27]2[CH:37]=[CH:36][C:30]([C:31]([N:33]([CH3:35])[CH3:34])=[O:32])=[CH:29][CH:28]=2)=[N:11][C:12]=1[C:13]1[O:14][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N+:24]([O-])=O)=[N:16][N:17]=1.C(=O)([O-])O.[Na+]>CCOC(C)=O.ClCCl>[NH2:6][C:7]1[N:8]=[CH:9][C:10]([C:27]2[CH:37]=[CH:36][C:30]([C:31]([N:33]([CH3:35])[CH3:34])=[O:32])=[CH:29][CH:28]=2)=[N:11][C:12]=1[C:13]1[O:14][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[NH2:24])=[N:16][N:17]=1

Participants

6

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 59471693HCID 59471693, compound

Product 1

HCID 59471998HCID 59471998, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

SnCl2.2H2O (151.6 mg, 0.6720 mmol) was added to a solution of 4-[5-amino-6-[5-(2-nitrophenyl)-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-N,N-dimethyl-benzamide (58 mg, 0.1344 mmol) in EtOAc (3 mL) and dichloromethane (1 mL) at room temperature and the resulting solution stirred overnight at room temperature. The reaction mixture was poured carefully onto saturated aqueous sodium hydrogen carbonate solution (5 mL) and the layers separated. The aqueous layer extracted further with dichloromethane (2×15 mL) and the combined organics dried over MgSO4 and concentrated in vacuo to leave a yellow solid. This was purified using by reverse phase preparative HPLC [Waters Sunfire C18, 10 mM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]. The product fractions were freeze dried to give the product as a yellow solid (17.2 mg, 34% yield); 1H NMR (400.0 MHz, DMSO) d 2.98 (m, 6H), 6.78 (t, 1H), 6.88 (br s, 1H), 7.34 (m, 1H), 7.55 (m, 2H), 7.79 (br s, 2H), 7.85 (m, 1H), 8.18 (m, 2H) and 8.99 (s, 1H) ppm; MS (ES+) 402.26

Workup

  1. customthe layers separated
  2. extractionThe aqueous layer extracted further with dichloromethane (2×15 mL)
  3. dry with materialthe combined organics dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customto leave a yellow solid
  6. customThis was purified
  7. customusing by reverse phase preparative HPLC [Waters Sunfire C18, 10 mM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]
  8. customdried

Sources & evidence

ORD record
ord-6fdb6d566865432fb82f0f6d574776a0
Source dataset
uspto-grants-2014_09
Patent number
US08841308B2

Reaction notes

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