2-Iodoxybenzoic acid → HCID 53258822, compound

HRID 2170880Notes

Reaction equation

HRID 2170880 reaction equation
I(C1C=CC=CC=1C(O)=O)(=O)=O.[OH:13][CH:14]([C:44]([NH:46][O:47][CH3:48])=[O:45])[CH:15]([NH:23][C:24](=[O:43])[C:25]1[CH:30]=[CH:29][CH:28]=[N:27][C:26]=1[N:31]1[CH:35]=[C:34]([CH3:36])[C:33]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[N:32]1)[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>ClCCl>[CH3:48][O:47][NH:46][C:44](=[O:45])[C:14](=[O:13])[CH:15]([NH:23][C:24]([C:25]1[C:26]([N:31]2[CH:35]=[C:34]([CH3:36])[C:33]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)=[N:32]2)=[N:27][CH:28]=[CH:29][CH:30]=1)=[O:43])[CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 1087942-Iodoxybenzoic acid2×HCID 86654645HCID 86654645, compound

Product 1

HCID 53258822HCID 53258822, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To polymer-supported IBX (Novabiochem, 1.1 mmol/g; 300 mg, 0.330 mmol) dichloromethane (5 ml) was added and the mixture was left for 10 min. Then N-(3-hydroxy-4-(methoxyamino)-4-oxo-1-phenylbutan-2-yl)-2-(4-methyl-3-phenyl-1H-pyrazol-1-yl)nicotinamide (77 mg, 0.159 mmol) in 10 ml of dichloromethane was added and the mixture was shaken for 1 day at room temperature. Additional portions of the polymer-supported IBX were added after 2 days and 3 days (120 mg, 0.132 mmol and 100 mg, 0.110 mmol). After 4 days the mixture was filtered off, evaporated under reduced pressure and the crude product purified via chromatography on silica gel (eluent: CH2Cl2+2-4% (v/v) methanol). After evaporation of the combined product fractions 45 mg of an amorphous solid were obtained. ESI-MS [M+H]+: 484.2

Workup

  1. filtrationAfter 4 days the mixture was filtered off
  2. customevaporated under reduced pressure
  3. customthe crude product purified via chromatography on silica gel (eluent: CH2Cl2+2-4% (v/v) methanol)
  4. customAfter evaporation of the combined product fractions 45 mg of an amorphous solid
  5. customwere obtained

Sources & evidence

ORD record
ord-c3b6797770d9445b9409c44a21679466
Source dataset
uspto-grants-2015_06
Patent number
US09051304B2

Reaction notes

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