Stannous Chloride → HCID 16718547, compound

HRID 1711101Notes

Reaction equation

HRID 1711101 reaction equation
[C:1]([C:3]1[S:11][C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[O:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][C:14]=2[F:22])[CH:4]=1)#[CH:2].Cl[Sn]Cl.[C:26]1([CH2:32][C:33]([N:35]=[C:36]=[S:37])=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CO.CCO.C1(C)C=CC=CC=1>[C:1]([C:3]1[S:11][C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[O:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:36]([NH:35][C:33](=[O:34])[CH2:32][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[S:37])=[CH:15][C:14]=2[F:22])[CH:4]=1)#[CH:2]

Participants

7

Reactant 3

HCID 24479Stannous ChlorideHCID 12454157Phenylacetyl isothiocyanateHCID 59457702HCID 59457702, compound

Product 1

HCID 16718547HCID 16718547, compoundYield 9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of the alkyne 410 (200 mg, 0.64 mmol) in MeOH (10 ml) was added SnCl2×2H2O (574 mg, 4 eq, 2.54 mmol) and the reaction mixture was heated to reflux for 3 hours. It was then cooled to RT, concentrated and crude amine 411 was used directly in the next step with no additional purification (182 mg, 100%). To a solution of 411 (182 mg, 0.64 mmol) in EtOH (2 ml) and toluene (6 ml) was added 2-phenylacetyl isothiocyanate (227 mg, 2 eq, 1.28 mmol) and the reaction mixture was stirred at RT for 2 hrs, concentrated under reduced pressure and the residue was purified by column chromatography (1:3 EtOAc:hexane) to afford 406 as a white solid (25 mg, 9% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 12.49 (s, 1H), 11.82 (s, 1H), 8.58 (d, J=5.48 Hz, 1H), 8.01 (m, 1H), 7.88 (s, 1H), 7.50 (m, 2H), 7.25 (m, 5H), 6.73 (d, J=5.48 Hz, 1H), 5.01 (s, 1H), 3.81 (s, 2H). LCMS: 462.2 (M+H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 3 hours
  3. concentrationconcentrated
  4. customcrude amine 411 was used directly in the next step with no additional purification (182 mg, 100%)
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified by column chromatography (1:3 EtOAc:hexane)

Sources & evidence

ORD record
ord-fac3830486f2479cbe41014494caec7f
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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