Water → HCID 69254958, compound

HRID 902679Notes

Reaction equation

HRID 902679 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14][NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[C:18]=2[Cl:27])[CH:6]=1.[S:29]1[CH:33]=[CH:32][C:31]([CH:34]([CH3:37])[CH:35]=O)=[CH:30]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCl.C(O)(=O)C>[CH3:1][O:2][C:3](=[O:28])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:25])([F:24])[F:26])[C:18]=2[Cl:27])[CH2:35][CH:34]([C:31]2[CH:32]=[CH:33][S:29][CH:30]=2)[CH3:37])[CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 5049666Sodium triacetoxyborohydrideHCID 12477281HCID 12477281, compoundHCID 69254653{3-[3-(2-chloro-3-trifluoromethyl-benzylamino)-propoxy]-phenyl}-acetic Acid Methyl Ester

Product 1

HCID 69254958HCID 69254958, compoundYield 54.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of {3-[3-(2-chloro-3-trifluoromethyl-benzylamino)-propoxy]-phenyl}-acetic acid methyl ester (70 mg, 0.17 mmol) in dry dichloromethane (20 ml) was added acetic acid (2 drops) followed by 2-thiophen-3-yl-propionaldehyde (26 mg, 0.19 mmol) and sodium triacetoxyborohydride (72 mg, 0.34 mmol). After the resulting mixture was stirred at room temperature overnight, water was added to quench the reaction. The aqueous layer was extracted with ethyl acetate. The combined organic layers was washed with brine, dried over sodium sulfate and concentrated in vacco. The crude mixture was purified by HPLC (YMC CombiPrep ODS-A, 50×20 mm, 20 mL/min, A: acetonitrile B: water, A: 60 to 100% during 10 min, UV detection at 254 nm) to give 50 mg (32% yield) of the title compound as an oil MS m/e 541.4 (M+H)+.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layers was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacco
  7. customThe crude mixture was purified by HPLC (YMC CombiPrep ODS-A, 50×20 mm, 20 mL/min
  8. waitA: acetonitrile B: water, A: 60 to 100% during 10 min

Sources & evidence

ORD record
ord-d4b835593c4d485b858d62c24246dee9
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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