Phenylacetyl isothiocyanate → 1-(3-Fluoro-4-(2-(2-furyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-3-(2-phenylacetyl)thiourea

HRID 1676289Notes

Reaction equation

HRID 1676289 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:23])[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][CH:20]=[CH:21][CH:22]=3)[S:17][C:10]=12.[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>>[F:1][C:2]1[CH:3]=[C:4]([NH:23][C:34]([NH:33][C:31](=[O:32])[CH2:30][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[S:35])[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][CH:20]=[CH:21][CH:22]=3)[S:17][C:10]=12

Participants

3

Reactant 2

HCID 12454157Phenylacetyl isothiocyanateHCID 673502153-Fluoro-4-(2-(furan-2-yl)thieno[3,2-b]pyridin-7-yloxy)benzenamine

Product 1

HCID 249832641-(3-Fluoro-4-(2-(2-furyl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-3-(2-phenylacetyl)thiourea

Procedure

Prepared from 3-fluoro-4-(2-(furan-2-yl)thieno[3,2-b]pyridin-7-yloxy)benzenamine (100 mg, 0.306 mmol) obtained in Step A and 2-phenylethanoyl isothiocyanate (109 mg, 0.613 mmol; prepared according to the procedure described by J. Org. Chem. 1964, 29, 1115-1119) using the procedure described for Example 96, Step D. Collected the product (6 mg, 4%) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 12.6 (s, 1H), 8.53 (s, 1H), 8.39 (d, J=6.6 Hz, 1H), 8.07 (d, J=13.2 Hz, 1H), 7.90 (s, 1H), 7.61 (d, J=6.2 Hz, 1H), 7.44 (m, 7H), 7.04 (s, 1H), 6.73 (d, J=6.2 Hz, 1H), 6.62 (s, 1H), 3.78 (s, 2H). LRMS (APCI+) m/e 504 (M+1) detected.

Workup

  1. customprepared
  2. customCollected the product (6 mg, 4%) as a white solid

Sources & evidence

ORD record
ord-6800566a9ed74510958174aeaba945d3
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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