Trifluoroacetic acid → HCID 11801169, compound

HRID 1387013Notes

Reaction equation

HRID 1387013 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([CH:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][N:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)=[CH:15][CH:14]=3)O)=[C:9]([C:28]3[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][N:37]4[CH2:41][CH2:40][CH2:39][CH2:38]4)=[CH:30][CH:29]=3)[S:8][C:7]=2[CH:42]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClC(Cl)C>[N:22]1([CH2:21][CH2:20][O:19][C:16]2[CH:17]=[CH:18][C:13]([CH2:11][C:10]3[C:6]4[CH:5]=[CH:4][C:3]([CH2:2][NH2:1])=[CH:42][C:7]=4[S:8][C:9]=3[C:28]3[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][N:37]4[CH2:38][CH2:39][CH2:40][CH2:41]4)=[CH:30][CH:29]=3)=[CH:14][CH:15]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 21182797HCID 21182797, compound

Product 1

HCID 11801169HCID 11801169, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 1.32 g (2.3 mmol) of 6-(aminomethyl)-α-[4-[2-(1-piperidinyl)ethoxy]phenyl]-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene-3-methanol in 40 mL of anhydrous dichloroethane at 0° C. was added 1.84 g (15.8 mmol) of triethylsilane and 2.62 g (23.0 mmol) of trifluoroacetic acid, respectively, under a nitrogen atmosphere. After one hour at 0° C., the reaction was warmed to room temperature and stirred for 24 h. The reaction was quenched with 10 mL of saturated aqueous sodium bicarbonate and poured into 30 mL of water. The aqueous layer was saturated with sodium chloride, separated from the dichloroethane layer, and extracted with three 50 mL portions of THF. The combined organic layers were dried over anhydrous magnesium sulfate and concentrated at reduced pressure to give 786 mg (60% crude yield) of a brown foam. This material was carried on to the salt in Part D.

Workup

  1. customThe reaction was quenched with 10 mL of saturated aqueous sodium bicarbonate
  2. additionpoured into 30 mL of water
  3. customseparated from the dichloroethane layer
  4. extractionextracted with three 50 mL portions of THF
  5. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  6. concentrationconcentrated at reduced pressure
  7. customto give 786 mg (60% crude yield) of a brown foam

Sources & evidence

ORD record
ord-472da6b83b734ee19efaafba8a1b24d8
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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