m-Tolyl isocyanate → HCID 131735813, compound

HRID 2205558Notes

Reaction equation

HRID 2205558 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:10]3[C:11]([NH2:25])=[N:12][CH:13]=[C:14]([B:16]4[O:20][C:19]([CH3:22])([CH3:21])[C:18]([CH3:24])([CH3:23])[O:17]4)[CH:15]=3)=[CH:7][C:6]=2[CH:26]=1.[C:27]1([CH3:36])[CH:32]=[CH:31][CH:30]=[C:29]([N:33]=[C:34]=[O:35])[CH:28]=1>C1COCC1>[NH2:25][C:11]1[C:10]([C:8]2[S:9][C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:34]([NH:33][C:29]4[CH:30]=[CH:31][CH:32]=[C:27]([CH3:36])[CH:28]=4)=[O:35])=[CH:26][C:6]=3[CH:7]=2)=[CH:15][C:14]([B:16]2[O:20][C:19]([CH3:22])([CH3:21])[C:18]([CH3:24])([CH3:23])[O:17]2)=[CH:13][N:12]=1

Participants

4

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 131735814HCID 131735814, compound

Product 1

HCID 131735813HCID 131735813, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 3-(5-amino-1-benzothien-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (734.6 mg, 2 mmol. 1 eq) in anhydrous THF (10 mL) at room temperature was added dropwise m-tolylisocyanate (0.251 mL, 1 eq). After the reaction was stirred at room temperature for 4 hours, it was partitioned between ethyl acetate and aqueous ammonium chloride. The organic layer was isolated, washed with saturated aqueous sodium bicarbonate, brine, and dried with anhydrous sodium sulfate. The upper solution layer was decanted, concentrated, and the solid residue was subject to a gradient column chromatography (DCM to MeOH-DCM 1:5). The products' fractions were collected, concentrated, the solid was triturated with EtOAc-Hex (1:7) yielding 1-{2-[2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl]-1-benzothien-5-yl}-3-(3-methylphenyl)urea as a white powder upon filtration in amount of 407 mg.

Workup

  1. customit was partitioned between ethyl acetate and aqueous ammonium chloride
  2. customThe organic layer was isolated
  3. washwashed with saturated aqueous sodium bicarbonate, brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe upper solution layer was decanted
  6. concentrationconcentrated
  7. customThe products' fractions were collected
  8. concentrationconcentrated
  9. customthe solid was triturated with EtOAc-Hex (1:7)

Sources & evidence

ORD record
ord-dcafc6c2b9ac4a1f9bc0fe70fc90fab8
Source dataset
uspto-grants-2016_06
Patent number
US09371314B2

Reaction notes

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