4-(2-(1-Ethyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamine → HCID 68697453, compound

HRID 1261371Notes

Reaction equation

HRID 1261371 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].[F:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH2:33][C:34]([N:36]=[C:37]=[O:38])=[O:35]>>[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:37]([NH:36][C:34](=[O:35])[CH2:33][C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=4[F:26])=[O:38])=[CH:20][C:19]=3[F:25])[CH:9]=2)[N:5]=[CH:4]1)[CH3:2]

Participants

3

Reactant 2

HCID 594244554-(2-(1-Ethyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamineHCID 83529831HCID 83529831, compound

Product 1

HCID 68697453HCID 68697453, compoundYield 42%

Procedure

A mixture of 308 (320 mg, 0.90 mmol) and (2-fluoro-phenyl)-acetyl isocyanate (600 mg, 3.35 mmol) [A. 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 309b in 42% yield as a white solid. 1H NMR (d-DMSO) δ (ppm): 11.10(s, 1H), 10.58(s, 1H), 8.42(d, 1H, J=5.5 Hz), 7.94(d, 1H, J=1.1 Hz), 7.82-7.77(m, 2H), 7.65(s, 1H), 7.45-7.30(m, 4H), 7.19-7.16(m, 2H), 6.54(dd, 1H, J1=0.7 Hz, J2=5.4 Hz), 4.04(q, 2H), 3.83(s, 2H), 1.38(t, 3H). MS (m/z): 534.1(M+H) (found).

Workup

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

Sources & evidence

ORD record
ord-70fb43b07d1e474ba8c2d49dc0418d7d
Source dataset
uspto-grants-2013_06
Patent number
US08470850B2

Reaction notes

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