Sodium Chlorite → HCID 178440927, compound

HRID 1640175Notes

Reaction equation

HRID 1640175 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12]([CH:14]2[CH2:23][CH2:22][C:21]3[C:16](=[CH:17][C:18]([O:24][C:25]4[CH:30]=[CH:29][N:28]=[C:27]([C:31]5[NH:32][CH:33]=[C:34]([CH:36]=[O:37])[N:35]=5)[CH:26]=4)=[CH:19][CH:20]=3)[CH2:15]2)=[O:13])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].Cl([O-])=[O:39].[Na+].P([O-])(O)(O)=O.[Na+]>CC(=CC)C.C(#N)C.C(O)(C)(C)C.O>[C:1]([C:5]1[CH:6]=[C:7]([NH:11][C:12]([CH:14]2[CH2:15][C:16]3[CH:17]=[C:18]([O:24][C:25]4[CH:30]=[CH:29][N:28]=[C:27]([C:31]5[NH:32][CH:33]=[C:34]([C:36]([OH:39])=[O:37])[N:35]=5)[CH:26]=4)[CH:19]=[CH:20][C:21]=3[CH2:22][CH2:23]2)=[O:13])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 3

HCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 178440925HCID 178440925, compound

Product 1

HCID 178440927HCID 178440927, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6386tert-ButanolSolventHCID 105532-Methyl-2-buteneSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of N-(3-tert-butylphenyl)-7-{[2-(4-formyl-1H-imidazol-2-yl)pyridin-4-yl]oxy}-1,2,3,4-tetrahydronaphthalene-2-carboxamide (570 mg, 1.2 mmol) in 2-methyl-2-butene (3 mL), acetonitrile (6 mL) and tert-butyl alcohol (6 mL) was cooled to 0° C. To this cold reaction mixture was added a solution of sodium chlorite (646 mg, 5.71 mmol) and sodium dihydrogenphosphate (680 mg, 5.6 mmol) in water (3 mL). The yellow solution was allowed to stir at 0° C. overnight. The reaction was quenched by the addition of brine (3 mL) and extracted with EtOAc (15 mL×3). The combined organic solutions were washed with brine and dried over Na2SO4, filtered and concentrated to give 2-{4-[(7-{[(3-tert-butylphenyl)amino]carbonyl}-5,6,7,8-tetrahydronaphthalen-2-yl)oxy]pyridin-2-yl}-1H-imidazole-4carboxylic acid (I-155), which was used without further purification. LCMS: (FA) ES+ 511.2.

Workup

  1. customTo this cold reaction mixture
  2. customThe reaction was quenched by the addition of brine (3 mL)
  3. extractionextracted with EtOAc (15 mL×3)
  4. washThe combined organic solutions were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-aa775f8f8e044a6296c3fb80c7723c4c
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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