Phenylacetyl isocyanate → N-(3-Fluoro-4-(2-(1-methyl-1H-imidazol-5-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl carbamoyl)-2-phenylacetamide

HRID 1711074Notes

Reaction equation

HRID 1711074 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:24])[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[N:22]([CH3:23])[CH:21]=[N:20][CH:19]=3)[S:17][C:10]=12.[C:25]1([CH2:31][C:32]([N:34]=[C:35]=[O:36])=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[F:1][C:2]1[CH:3]=[C:4]([NH:24][C:35]([NH:34][C:32](=[O:33])[CH2:31][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:36])[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[N:22]([CH3:23])[CH:21]=[N:20][CH:19]=3)[S:17][C:10]=12

Participants

3

Reactant 2

HCID 12259960Phenylacetyl isocyanateHCID 594244313-Fluoro-4-(2-(1-methyl-1H-imidazol-5-yl)thieno[3,2-b]pyridin-7-yloxy)benzenamine

Product 1

HCID 59424468N-(3-Fluoro-4-(2-(1-methyl-1H-imidazol-5-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl carbamoyl)-2-phenylacetamideYield 42%

Procedure

A mixture of 306 (99 mg, 0.29 mmol) and 2-phenylacetyl isocyanate (97 mg, 0.60 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 (10:90) to afford the title compound 307 (42% yield) as a white solid. 1H NMR (d-DMSO) δ (ppm): 11.11 (s, 1H), 10.68 (s, 1H, J=5.5 Hz), 8.49(d), 7.85 (s, 1H), 7.82(dd, 1H, J1=12.9 Hz, J2=2.4 Hz), 7.76 (s, 1H), 7.43 (m, 2H), 7.40 (s, 1H), 7.32 (m, 4H), 7.28 (m, 1H), 6.61(d, 1H, J=5.5 Hz), 3.89 (s, 3H), 3.74 (s, 2H). MS (m/z): 502.4 (M+H) (found).

Workup

  1. washgradient eluted with EtOAc, to MeOH/EtOAc (10:90)

Sources & evidence

ORD record
ord-8d449e743a484a5e9b725f708f448bec
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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