Phenylacetyl isocyanate → N-(4-(2-(1-Ethyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl carbamoyl)-2-phenylacetamide

HRID 1711075Notes

Reaction equation

HRID 1711075 reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[S:16][C:15]3[C:10](=[N:11][CH:12]=[CH:13][C:14]=3[O:17][C:18]3[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][C:19]=3[F:25])[CH:9]=2)[N:5]=[CH:4]1)[CH3:2].[C:26]1([CH2:32][C:33]([N:35]=[C:36]=[O:37])=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[S:16][C:15]3[C:10](=[N:11][CH:12]=[CH:13][C:14]=3[O:17][C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:36]([NH:35][C:33](=[O:34])[CH2:32][C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)=[O:37])=[CH:20][C:19]=3[F:25])[CH:9]=2)[N:5]=[CH:4]1)[CH3:2]

Participants

3

Reactant 2

HCID 12259960Phenylacetyl isocyanateHCID 594244554-(2-(1-Ethyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamine

Product 1

HCID 68698242N-(4-(2-(1-Ethyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorophenyl carbamoyl)-2-phenylacetamideYield 45%

Procedure

A mixture of 308 (300 mg, 0.85 mmol) and 2-phenylacetyl isocyanate (164 mg, 1.02 mmoL) [Arthur J. Hill et al. JACS, 62; 1940; 1595] was stirred for 1 h at room temperature, loaded directly onto a flash chromatography column and gradient eluted with EtOAc, to MeOH/EtOAc (20:80) to afford the title compound 309a (45% yield) as a white solid. 1H NMR (d-DMSO) δ (ppm): 11.07 (s, 1H), 10.63 (s, 1H), 8.41(d, 1H, J=5.5 Hz), 7.94(d, 1H, J=1.4 Hz), 7.80(dd, 1H, J1=13.1 Hz, J2=2.4 Hz), 7.77(d, 1H, J=1.1 Hz), 7.65 (s, 1H), 7.46-7.39 (s, 2H), 7.35-7.19 (m, 4H), 7.28-7.24 (m, 1H), 6.54(dd, 1H, J1=5.5 Hz, J2=0.8 Hz), 4.03(q, 2H), 3.73 (s, 2H), 1.38(t, 3H). MS (m/z): 516.1 (M+H) (found).

Workup

  1. washgradient eluted with EtOAc, to MeOH/EtOAc (20:80)

Sources & evidence

ORD record
ord-99f57f19f0384cc28c534de1ab56bc17
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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