Tert-Butyl nitrite → HCID 68721995, compound

HRID 1875204Notes

Reaction equation

HRID 1875204 reaction equation
N[C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9]#[N:10])=[CH:4][C:3]=1[O:11][C:12]1[C:13]([F:37])=[C:14]([CH2:19][NH:20][C:21]([C:23]2[N:27]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[CH:26]=[N:25][C:24]=2[Cl:36])=[O:22])[CH:15]=[CH:16][C:17]=1[Cl:18].N(OC(C)(C)C)=O>C(#N)C.CCOC(C)=O>[Cl:36][C:24]1[N:25]=[CH:26][N:27]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[C:23]=1[C:21]([NH:20][CH2:19][C:14]1[CH:15]=[CH:16][C:17]([Cl:18])=[C:12]([O:11][C:3]2[CH:2]=[CH:7][C:6]([F:8])=[C:5]([C:9]#[N:10])[CH:4]=2)[C:13]=1[F:37])=[O:22]

Participants

5

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 68722215HCID 68722215, compound

Product 1

HCID 68721995HCID 68721995, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 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 (110 mg, 0.194 mmol) in Acetonitrile (8 ml) was added tert butyl nitrite (0.046 ml, 0.387 mmol) and the reaction mixture was stirred at RT for 1 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 4-chloro-N-({4-chloro-3-[(3-cyano-4-fluorophenyl)oxy]-2-fluorophenyl}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (49 mg, 0.089 mmol, 46% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.76 (t, 1H), 7.98 (s, 1H), 7.42-7.59 (m, 3H), 7.29-7.42 (m, 2H), 5.49 (s, 2H), 4.48 (d, 2H), 3.38 (t, 2H), 0.75 (t, 2 H), −0.09 (s, 9H).

Workup

  1. washwashed with water
  2. customThe solvent was removed
  3. customthe crude material was purified via silica gel chromatography

Sources & evidence

ORD record
ord-4e96f554c7724816b079d110c81caa08
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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