Phenylacetyl isothiocyanate → HCID 24983252, compound

HRID 1676285Notes

Reaction equation

HRID 1676285 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:31])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([C:18]3[O:19][C:20]([CH2:23][N:24]4[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]4)=[CH:21][CH:22]=3)[S:17][C:10]=12.C1(C)C=CC=CC=1.C(O)C.[C:42]1([CH2:48][C:49]([N:51]=[C:52]=[S:53])=[O:50])[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([NH:31][C:52]([NH:51][C:49](=[O:50])[CH2:48][C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)=[S:53])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([C:18]3[O:19][C:20]([CH2:23][N:24]4[CH2:25][CH2:26][N:27]([CH3:30])[CH2:28][CH2:29]4)=[CH:21][CH:22]=3)[S:17][C:10]=12

Participants

5

Reactant 3

HCID 12454157Phenylacetyl isothiocyanateHCID 21863594Toluene ethanolHCID 67345312HCID 67345312, compound

Product 1

HCID 24983252HCID 24983252, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a 5 mL round bottom flask was added 3-fluoro-4-(2-(5-((4-methylpiperazin-1-yl)methyl)furan-2-yl)thieno[3,2-b]pyridin-7-yloxy)benzenamine (32 mg, 0.0713 mmol) and 1:1 toluene/ethanol (1 mL). 2-Phenylethanoyl isothiocyanate (25.3 mg, 0.143 mmol; prepared according to the procedure described by J. Org. Chem. 1964, 29, 1115-1119) was added as a solution in toluene (0.5 mL). After stirring for 30 minutes at room temperature, the crude was concentrated in vacuo. The crude was dissolved in MeOH and purified by preparative TLC, eluting with 9:1 CH2Cl2/MeOH. The product was collected at Rf 0.4 just above the unreacted starting material at Rf 0.3 to provide the product (5 mg, 10%) as a white solid. LRMS (APCI+) m/e 626 (M+1) detected; 1H NMR (CDCl3, 400 MHz) δ 9.98 (s, 1H), 8.45 (d, J=5.5 Hz, 1H), 8.22 (s, 1H), 7.75 (d, J=13.7 Hz, 1H), 7.62 (s, 1H), 7.45 (m, 2H), 7.24 (m, 2H), 7.07 (t, J=8.6 Hz, 2H), 6.71 (s, 1H), 6.35 (s, 1H), 3.66 (s, 2H), 2.58 (m, 8H), 2.29 (s, 3H), 1.79 (m, 4H).

Workup

  1. customprepared
  2. concentrationthe crude was concentrated in vacuo
  3. dissolutionThe crude was dissolved in MeOH
  4. custompurified by preparative TLC
  5. washeluting with 9:1 CH2Cl2/MeOH
  6. customThe product was collected at Rf 0.4 just above the

Sources & evidence

ORD record
ord-8efdbe3b883a48ca9868399dd21d764f
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

Loading…