Dichloromethane → HCID 66876691, compound

HRID 2192513Notes

Reaction equation

HRID 2192513 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:18]=3[CH:19]=[CH:20][N:21]=[C:22]4[N:27]3[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]3)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[F:40][C:41]([F:46])([F:45])[C:42]([OH:44])=[O:43].ClCCl>CS(C)=O>[F:40][C:41]([F:46])([F:45])[C:42]([OH:44])=[O:43].[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:18]=3[CH:19]=[CH:20][N:21]=[C:22]4[N:27]3[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]3)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 58149909HCID 58149909, compound

Product 1

HCID 66876691HCID 66876691, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1,1-Dimethylethyl 4-[5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-isoquinolinyl]-1-piperazinecarboxylate (D15; 24 mg, 0.044 mmol), trifluoroacetic acid (1 ml, 13.0 mmol) and dichloromethane (1 ml) were stirred at room temperature for 1 h. The samples were dissolved in DMSO (1 ml) and purified by Mass Directed Preparative HPLC (supelcosil ABZ+Plus alkylamide phase column), eluting with solvents A/B (A: water+0.1% formic acid, B: MeCN:Water 95:5+0.05% formic acid). The solvent was evaporated in vacuo to give the title compound as a white solid (16 mg).

Workup

  1. custompurified by Mass Directed Preparative HPLC (supelcosil ABZ+Plus alkylamide phase column)
  2. washeluting with solvents A/B (A: water+0.1% formic acid, B
  3. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-7b8594b341c64da7b358def846d34d3c
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

Loading…