Toluene → 2-phenyl-N-{[(4-{[1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]oxy}phenyl) amino]carbonothioyl}acetamide

HRID 1011295Notes

Reaction equation

HRID 1011295 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:11]2=[N:12][CH:13]=[N:14][C:15]([O:16][C:17]3[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=3)=[C:10]2[CH:9]=[N:8]1.C1(C)C=CC=CC=1.[C:31]1([CH2:37][C:38]([N:40]=[C:41]=[S:42])=[O:39])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(O)C>[C:31]1([CH2:37][C:38]([NH:40][C:41]([NH:23][C:20]2[CH:21]=[CH:22][C:17]([O:16][C:15]3[N:14]=[CH:13][N:12]=[C:11]4[N:7]([CH:2]5[CH2:3][CH2:4][CH2:5][CH2:6][O:1]5)[N:8]=[CH:9][C:10]=34)=[CH:18][CH:19]=2)=[S:42])=[O:39])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 12454157Phenylacetyl isothiocyanateHCID 589380164-[1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-phenylamine

Product 1

HCID 116916472-phenyl-N-{[(4-{[1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]oxy}phenyl) amino]carbonothioyl}acetamideYield 55.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a round bottom flask equipped with a magnetic stir bar was added 4-[1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-phenylamine (0.199 g, 0.63 mmol, 1.0 eq.), toluene (10 ml), ethanol (10 ml) and phenyl-acetyl isothiocyanate (0.33 g, 2.0 mmol, 3.0 eq). The reaction mixture was stirred at room temperature overnight. After removal of solvent in vacuo, the product was separated by flash chromatography using a 3:1 hexane/ethyl acetate solution as the eluent to give 2-phenyl-N-{[(4-{[1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]oxy}phenyl)amino]carbonothioyl}acetamide (0.17 g, 54% yield). 1H NMR (400 MHz, DMSO): 12.39 (s, 1H), 11.78 (s, 1H), 8.59 (s, 1H), 8.20 (s, 1H), 7.71 (d, 2H), 7.53 (t, 1H), 7.34 (m, 5H), 7.26 (m, 1H), 5.97 (d, 1H), 3.94 (d, 1H), 3.73 (s, 2H), 3.72 (m 1H), 3.40 (s, 2H), 2.05 (m, 1H), 1.93 (m, 1H), 1.77 (m, 1H), 1.58 (m, 1H); MS (ESI) for C25H24N6O3S: 489 (MH+).

Workup

  1. customTo a round bottom flask equipped with a magnetic stir bar
  2. customAfter removal of solvent in vacuo
  3. customthe product was separated by flash chromatography

Sources & evidence

ORD record
ord-5b0f3d039d7f462ab5ae0c0620159e29
Source dataset
uspto-grants-2011_07
Patent number
US07977345B2

Reaction notes

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