HCID 86657450, compound → HCID 86657449, compound

HRID 2096615Notes

Reaction equation

HRID 2096615 reaction equation
[OH:1][C:2]([C:4]([F:7])([F:6])[F:5])=[O:3].[NH2:8][C:9]1[N:10]([CH3:38])[C:11](=[O:37])[C:12]2([N:36]=1)[C:21]1[C:16](=[CH:17][CH:18]=[C:19]([C:22]3[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=3)[C:25]#[N:26])[CH:20]=1)[S:15][CH:14]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:13]2>CO.O>[OH:3][C:2]([C:4]([F:7])([F:6])[F:5])=[O:1].[NH2:8][C:9]1[N:10]([CH3:38])[C:11](=[O:37])[C:12]2([N:36]=1)[C:21]1[C:16](=[CH:17][CH:18]=[C:19]([C:22]3[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=3)[C:25]#[N:26])[CH:20]=1)[S:15](=[O:1])[CH:14]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[CH2:13]2

Participants

4

Reactant 1

HCID 86657450HCID 86657450, compound

Product 1

HCID 86657449HCID 86657449, compoundYield 115.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3-(2-amino-1-methyl-5-oxo-2′-phenyl-1,5-dihydrospiro[imidazole-4,4′-thiochroman]-6′-yl)benzonitrile TFA salt (27 mg, 0.05 mmol) in MeOH (5 mL) and H2O (0.1 mL) is added NaIO4 (21.4 mg, 0.10 mmol). The resulting mixture is stirred overnight at rt, then purified by preparative HPLC to give 3-(2-amino-1-methyl-1′,5-dioxo-2′-phenyl-1,5-dihydrospiro[imidazole-4,4′-thiochroman]-6′-yl)benzonitrile TFA salt (16 mg) with 5 mg of recovered starting material. MS ESI +ve m/z 441 (M+H)+.

Workup

  1. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-f3a11d0c9a984034a695b64d0065591e
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

Loading…