Iodine → 1-[3-tert-butyl-1-(4-fluorophenyl)pyrazol-5-yl]-3-[4-[(1-methyl-2-oxo-3H-imidazo[4,5-b]pyridin-7-yl)oxy]phenyl]urea

HRID 1864656Notes

Reaction equation

II.[NH2:3][C:4]1[CH:21]=[CH:20][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]3[NH:15][C:16](=[O:19])[N:17]([CH3:18])[C:10]=23)=[CH:6][CH:5]=1.[C:22]([C:26]1[CH:30]=[C:29]([NH:31][C:32](=O)[O:33]C2C=CC=CC=2)[N:28]([C:41]2[CH:46]=[CH:45][C:44]([F:47])=[CH:43][CH:42]=2)[N:27]=1)([CH3:25])([CH3:24])[CH3:23]>>[CH3:18][N:17]1[C:10]2[C:11](=[N:12][CH:13]=[CH:14][C:9]=2[O:8][C:7]2[CH:20]=[CH:21][C:4]([NH:3][C:32]([NH:31][C:29]3[N:28]([C:41]4[CH:46]=[CH:45][C:44]([F:47])=[CH:43][CH:42]=4)[N:27]=[C:26]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:30]=3)=[O:33])=[CH:5][CH:6]=2)[NH:15][C:16]1=[O:19]

Participants

Reactant 3

HCID 807Iodine

HCID 42626124HCID 42626124, compound

HCID 46196891Phenyl 3-tert-butyl-1-(4-fluorophenyl)-1h-pyrazol-5-ylcarbamate

Product 1

HCID 116349291-[3-tert-butyl-1-(4-fluorophenyl)pyrazol-5-yl]-3-[4-[(1-methyl-2-oxo-3H-imidazo[4,5-b]pyridin-7-yl)oxy]phenyl]ureaYield 35%

Procedure

Method I2 was used with 7-(4-aminophenoxy)-1-methyl-1H-imidazo[4,5-b]pyridin-2(3H)-one (25 mg, 0.1 mmol) and phenyl 3-tert-butyl-1-(4-fluorophenyl)-1H-pyrazol-5-yl-carbamate (42 mg, 0.12 mmol) to afford the title compound (18 mg, 35%). 1H-NMR (δ, ppm, DMSO-d6): 1.29 (s, 9H, t-Bu), 3.46 (s, 3H, CH3N), 6.37 (s, 1H, HPyz,4), 6.41 (d, 1H, HPy,6), 7.13 (d, 2H, Harom,Ph,3+5), 7.38 (t, 2H, Harom,4-F-Ph,3+5), 7.48 (d, 2H, Harom,Ph,2+6), 7.57 (dd, 2H, Harom,4-F-Ph,2+6), 7.80 (d, 1H, HPy,6), 8.38 (s, 1H, NHurea), 9.08 (s, 1H, NHurea), 11.61 (bs, 1H, NHPy3). LC-MS (m/z): 516 (M+H, 100). Acc. mass (C27H26N7O3F): calculated 516.2159, found 516.2086.

Sources & evidence

ORD record: ord-3bafbeaa6288400597465930fb4c263b
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625922B2

Reaction notes

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