Water → HCID 68722215, compound

HRID 1875202Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[CH:4][N:5]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[C:6]=1[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([O:18][C:19]2[CH:24]=[C:23]([C:25]#[N:26])[C:22]([F:27])=[CH:21][C:20]=2[N+:28]([O-])=O)[C:12]=1[F:31])=[O:8].S(S([O-])=O)([O-])=O.[Na+].[Na+].O>C1COCC1.CCOC(C)=O>[NH2:28][C:20]1[CH:21]=[C:22]([F:27])[C:23]([C:25]#[N:26])=[CH:24][C:19]=1[O:18][C:13]1[C:12]([F:31])=[C:11]([CH2:10][NH:9][C:7]([C:6]2[N:5]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:37])([CH3:38])[CH3:39])[CH:4]=[N:3][C:2]=2[Cl:1])=[O:8])[CH:16]=[CH:15][C:14]=1[Cl:17]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-chloro-N-({4-chloro-3-[(5-cyano-4-fluoro-2-nitrophenyl)oxy]-2-fluorophenyl}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (450 mg, 0.752 mmol) in THF (3 ml) was added sodium hydrosulfite (85% tech.) (924 mg, 4.51 mmol) in solution of Water (6.00 ml) and the reaction mixture was stirred at 60° C. for one hour. The reaction mixture was diluted with EtOAc and washed with water. The solvent was removed and the crude material was purified via silica gel chromatography to give N-({3-[(2-amino-5-cyano-4-fluorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)-4-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (386 mg, 0.679 mmol, 90% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.76 (t, 1H), 7.98 (s, 1H), 7.39-7.49 (m, 1H), 7.34 (t, 1H), 6.70 (s, 2H), 6.56-6.68 (m, 2H), 5.49 (s, 2H), 4.47 (d, 2H), 3.39 (t, 2H), 0.75 (t, 2H), −0.08 (s, 9H).

Workup

washwashed with water
customThe solvent was removed
customthe crude material was purified via silica gel chromatography

Sources & evidence

ORD record: ord-511ef2e4cab8415c9217ecb0cb63d014
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304419B2

Reaction notes

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