Trifluoroacetic acid → HCID 9908806, compound

HRID 843143Notes

Reaction equation

HRID 843143 reaction equation
[CH:1]([NH:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[C:14]2[C:15]([CH3:20])=[C:16]([CH2:18]O)[O:17][C:13]=2[CH:12]=[CH:11][CH:10]=1)([CH3:3])[CH3:2].[CH2:21]([SH:29])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:1]([NH:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[C:14]2[C:15]([CH3:20])=[C:16]([CH2:18][S:29][CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:17][C:13]=2[CH:12]=[CH:11][CH:10]=1)([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 781262-PhenylethanethiolHCID 22614949HCID 22614949, compound

Product 1

HCID 9908806HCID 9908806, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [4-(3-isopropylamino-propoxy)-3-methyl-benzofuran-2-yl]-methanol (14 mg, 0.05 mmol) and phenethyl mercaptan (10.3 mg, 0.075 mmol) in anhydrous CH2Cl2 (0.9 ml) was added TFA (0.2 ml). The Mixture was stirred at room temperature for 2.5 hours. The solvent was removed in vacuo. The residue was purified over preparative TLC (CH2Cl2/MeOH=100/1) to give desired compound (15 mg, 74%). FAB-MS: m/z 398 (MH+); 1H-NMR (CDCl3): δ 1.11 (6H, d, J=6.2 Hz), 2.05 (2H, m), 2.34 (3H, s), 2.61-2.96 (7H, m), 3.80 (2H, s), 4.11 (2H, m), 6.56 (1H, m), 6.95-7.28 (7H, m).

Workup

  1. customThe solvent was removed in vacuo
  2. customThe residue was purified over preparative TLC (CH2Cl2/MeOH=100/1)

Sources & evidence

ORD record
ord-f199c5e099994c0db4624fe3fefebd12
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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