Phenylacetyl isothiocyanate → 1-(4-(2-(Methylthio)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-3-(2-phenylacetyl)thiourea

HRID 1261301Notes

Reaction equation

HRID 1261301 reaction equation
[CH3:1][S:2][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]([NH2:19])=[CH:15][C:14]=2[F:20])[CH:4]=1.[C:21]1([CH2:27][C:28]([N:30]=[C:31]=[S:32])=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1>[CH3:1][S:2][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:31]([NH:30][C:28](=[O:29])[CH2:27][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[S:32])=[CH:15][C:14]=2[F:20])[CH:4]=1

Participants

4

Reactant 2

HCID 12454157Phenylacetyl isothiocyanateHCID 594244654-(2-(Methylthio)thieno[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamine

Product 1

HCID 249017001-(4-(2-(Methylthio)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl)-3-(2-phenylacetyl)thioureaYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 231 (61 mg) in THF (2 mL) was added 2-phenylacetyl isothiocyanate (42 mg, 0.199 mmol). The reaction mixture was stirred for 3 hours, concentrated under reduced pressure and the residue was purified by column chromatography, eluent EtOAc/hexane (35:65), to produce yellow oil. Purification of this material by preparative HPLC (column C-18 Aquasil, gradient: 60% MeOH to 95% MeOH) afforded title compound 232a (25 mg, 26% yield) as a cream solid. Characterization of 232a is provided in the table 22.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customthe residue was purified by column chromatography, eluent EtOAc/hexane (35:65)
  3. customto produce yellow oil
  4. customPurification of this material by preparative HPLC (column C-18 Aquasil, gradient: 60% MeOH to 95% MeOH)

Sources & evidence

ORD record
ord-7ee94c2ddd7547ffb0e577403955a512
Source dataset
uspto-grants-2013_06
Patent number
US08470850B2

Reaction notes

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