Trifluoroacetic acid → HCID 58338568, compound

HRID 445208Notes

Reaction equation

HRID 445208 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:16][CH:15]=1)=[C:8]([C:29]1[S:33][C:32]([C:34](O)([CH3:36])[CH3:35])=[CH:31][CH:30]=1)[CH:7]=[CH:6]2.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[CH:34]([C:32]1[S:33][C:29]([C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=3)[C:9]=2[O:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:18][CH:19]=2)=[CH:30][CH:31]=1)([CH3:36])[CH3:35]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 583385642-(5-(6-Methoxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)naphthalen-2-yl)thiophen-2-yl)propan-2-ol

Product 1

HCID 58338568HCID 58338568, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add 2-(5-(6-methoxy-1-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)naphthalen-2-yl)thiophen-2-yl)propan-2-ol (84 mg; 0.16 mmol), triethylsilane (1.7 mL) and dichloromethane (0.85 mL) to a flask under argon. Add trifluoroacetic acid (0.81 mL) and stir the resulting mixture for 45 minutes. Load the mixture onto an SCX acidic ion exchange column. Flush the column with 1:2 methanol/dichloromethane and elute with 1:2 2M ammonia in methanol/dichloromethane. Concentrate the ammonia containing eluent in vacuo to give the title compound (73.1 mg; 0.15 mmol): Mass spectrum (m/z): 502 (M+1).

Workup

  1. customFlush the column with 1:2 methanol/dichloromethane
  2. washelute with 1:2 2M ammonia in methanol/dichloromethane
  3. concentrationConcentrate the ammonia containing eluent in vacuo

Sources & evidence

ORD record
ord-52fda225e8b34169b3c9ffa80c70d7b5
Source dataset
uspto-grants-2013_07
Patent number
US08476300B2

Reaction notes

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