Stannous chloride dihydrate → HCID 11462963, compound

HRID 2242920Notes

Reaction equation

HRID 2242920 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([N:23]=[C:24]([C:26]3[O:27][CH:28]=[CH:29][CH:30]=3)[N:25]=2)[CH:5]=[C:6]([C:8]#[C:9][C:10]([CH3:22])([OH:21])[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)[N:7]=1.O.O.Cl[Sn]Cl>CN(C=O)C>[NH2:1][C:2]1[C:3]2[N:4]([N:23]=[C:24]([C:26]3[O:27][CH:28]=[CH:29][CH:30]=3)[N:25]=2)[CH:5]=[C:6]([C:8]#[C:9][C:10]([CH3:22])([OH:21])[CH2:11][C:12]2[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=2)[N:7]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 11235087HCID 11235087, compound

Product 1

HCID 11462963HCID 11462963, compoundYield 39.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(8-amino-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl)-2-methyl-1-(4-nitro-phenyl)-but-3-yn-2-ol-(17.7 mg, 0.044 mmol;. see Ex. 72 below which was prepared according to Example 24 above) in DMF (3 mL) was added SnCl2.2H2O (98 mg, 0.43 mmol) and the reaction was stirred at room temperature for overnight. The solvent was removed in vacuo and the residue was purified by reversed phase HPLC eluting with a water/acetonitrile gradient to yield the title compound (6.5 mg, 39%) as yellow solid. 1H NMR (300 MHz, DMSO) δ 8.25 (s, 1H), 7.93 (br s, 1 H), 7.60 (s, 2H), 7.33 (m, 2H), 7.14 (br s, 1H), 7.04 (m, 2H), 6.72 (br s, 1H), 2.82 (s, 2H), 1.38 (s,3 H). MS: m/z=375 amu (M++H).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by reversed phase HPLC
  3. washeluting with a water/acetonitrile gradient

Sources & evidence

ORD record
ord-55411b3e060a484187608e53a335c5d5
Source dataset
uspto-grants-2010_03
Patent number
US07674791B2

Reaction notes

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