Tert-Butyl nitrite → HCID 178510242, compound

HRID 1875206Notes

Reaction equation

HRID 1875206 reaction equation
N[C:2]1[C:7]([Cl:8])=[C:6]([F:9])[C:5]([C:10]#[N:11])=[CH:4][C:3]=1[O:12][C:13]1[C:14]([F:30])=[C:15]([CH2:20][NH:21][C:22]([C:24]2[NH:28][CH:27]=[N:26][C:25]=2[Cl:29])=[O:23])[CH:16]=[CH:17][C:18]=1[Cl:19].N(OC(C)(C)C)=O>C(#N)C>[Cl:29][C:25]1[N:26]=[CH:27][NH:28][C:24]=1[C:22]([NH:21][CH2:20][C:15]1[CH:16]=[CH:17][C:18]([Cl:19])=[C:13]([O:12][C:3]2[CH:4]=[C:5]([C:10]#[N:11])[C:6]([F:9])=[C:7]([Cl:8])[CH:2]=2)[C:14]=1[F:30])=[O:23]

Participants

4

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 178510245HCID 178510245, compound

Product 1

HCID 178510242HCID 178510242, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-({3-[(2-amino-3-chloro-5-cyano-4-fluorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)-4-chloro-1H-imidazole-5-carboxamide (38 mg, 0.080 mmol) in Acetonitrile (10 ml) was added tert-butyl nitrite (0.021 ml, 0.161 mmol) and the reaction mixture was stirred at RT for 2 hours. The reaction was quenched with methanol, the solvent was removed and the crude material was purified via reverse phase HPLC to give 4-chloro-N-({4-chloro-3-[(3-chloro-5-cyano-4-fluorophenyl)oxy]-2-fluorophenyl}methyl)-1H-imidazole-5-carboxamide (17 mg, 0.037 mmol, 46% yield). 1H NMR (DMSO-d6) δ ppm 8.25 (br. s., 1H) 7.74 (s, 1H) 7.69 (dd, 1H) 7.60 (t, 1H) 7.45 (d, 1H) 7.32 (t, 1H) 4.48 (d, 2H). LC-MS (ES+) m/z 457.05, [M+H].

Workup

  1. customThe reaction was quenched with methanol
  2. customthe solvent was removed
  3. customthe crude material was purified via reverse phase HPLC

Sources & evidence

ORD record
ord-284fdb8ac48144c4aa4dfe9fd74acdb4
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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