Phenylacetyl isothiocyanate → HCID 11554915, compound

HRID 1011308Notes

Reaction equation

HRID 1011308 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[CH:15]=[N:14][C:13]2[C:8]1=[N:9][CH:10]=[N:11][C:12]=2[O:16][C:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=1.[C:24]1([CH2:30][C:31]([N:33]=[C:34]=[S:35])=[O:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)Cl>[C:24]1([CH2:30][C:31]([NH:33][C:34]([NH:23][C:20]2[CH:21]=[CH:22][C:17]([O:16][C:12]3[N:11]=[CH:10][N:9]=[C:8]4[C:13]=3[N:14]=[CH:15][N:7]4[CH:2]3[CH2:3][CH2:4][CH2:5][CH2:6][O:1]3)=[CH:18][CH:19]=2)=[S:35])=[O:32])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 12454157Phenylacetyl isothiocyanateHCID 58938018HCID 58938018, compound

Product 1

HCID 11554915HCID 11554915, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a round bottom flask equipped with a magnetic stir bar was added 4-[9-(Tetrahydro-pyran-2-yl)-9H-purin-6-yloxy]-phenylamine (1.1 g, 3.60 mmol, 1.0 eq.), DCM (10 ml) and phenyl-acetyl isothiocyanate (0.643 g, 3.60 mmol, 1 eq). The reaction mixture was stirred at room temperature overnight. After removal of the solvent the product was purified by flash column chromatography on silica gel to give 2-phenyl-N-{[(4-{[9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl]oxy}phenyl)amino]-carbonothioyl}acetamide as a white solid (400 mg, 25% yield). 1H NMR (400 MHz, CDCl3): δ 12.40 (s, 1H), 8.80 (s; 1H), 8.60 (s, 1H), 8.30 (s, 1H), 7.80 (m, 2H), 7.20 (m, 7H), 5.9 (m, 1H), 4.20 (m, 1H), 3.8 (m, 2H), 2.20 (m, 3H), 1.80 (m, 4H). MS (ESI) for C25H24N6O3S: 489 (MH+).

Workup

  1. customTo a round bottom flask equipped with a magnetic stir bar
  2. customAfter removal of the solvent the product
  3. customwas purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-6fbe804103bb4b35ab42a95f63db3e32
Source dataset
uspto-grants-2011_07
Patent number
US07977345B2

Reaction notes

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