Toluene → N-({[3-fluoro-4-(7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)phenyl]amino}carbonothioyl)-2-phenylacetamide

HRID 1011291Notes

Reaction equation

HRID 1011291 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:18])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:10]2[CH:17]=[CH:16][NH:15][C:11]=2[N:12]=[CH:13][N:14]=1.C1(C)C=CC=CC=1.[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>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([NH:18][C:36]([NH:35][C:33](=[O:34])[CH2:32][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[S:37])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:10]2[CH:17]=[CH:16][NH:15][C:11]=2[N:12]=[CH:13][N:14]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 12454157Phenylacetyl isothiocyanateHCID 589380223-fluoro-4-(7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)-phenylamine

Product 1

HCID 58938015N-({[3-fluoro-4-(7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)phenyl]amino}carbonothioyl)-2-phenylacetamideYield 490.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a round bottom flask equipped with a magnetic stir bar was added 3-fluoro-4-(7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)-phenylamine (0.07 g, 0.29 mmol, 1.0 eq.), toluene (10 ml), ethanol (10 ml) and phenyl-acetyl isothiocyanate (0.22 g, 1.3 mmol, 4.5 eq). The reaction mixture was stirred at room temperature overnight. After removal of the solvent the product was precipitated from methanol to give N-({[3-fluoro-4-(7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)phenyl]amino}carbonothioyl)-2-phenylacetamide as a white solid (0.6 g, 50% yield). 1H NMR (400 MHz, DMSO): 12.49 (s, 1H), 12.35 (s, 1H), 12.82 (s, 1H), 8.32 (s, 1H), 7.89 (dd, 1H), 7.53 (t, 1H), 7.42 (d, 2H), 7.34 (d, 4H), 7.29 (m, 1H), 7.19 (d, 1H), 6.64 (d, 1H), 3.82 (s, 2H); MS (ESI) for C21H16FN5O2S: 422 (MH+).

Workup

  1. customTo a round bottom flask equipped with a magnetic stir bar
  2. customAfter removal of the solvent the product
  3. customwas precipitated from methanol

Sources & evidence

ORD record
ord-ae5e33ef3e4f4456a582db607d5d125f
Source dataset
uspto-grants-2011_07
Patent number
US07977345B2

Reaction notes

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