Tetrahydrofuran → N-acetyl-N1-[4-(4-ethyl-2-hydroxyphenoxy)-3-fluorophenyl]propan-1,3-diamine

HRID 626073Notes

Reaction equation

HRID 626073 reaction equation
[C:1]([N:4]([C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH3:23])=[CH:18][C:17]=2[O:24]CC2C=CC=CC=2)=[C:11]([F:32])[CH:10]=1)[CH2:5][CH2:6][CH2:7][NH2:8])(=[O:3])[CH3:2].O1CCCC1>CO>[C:1]([N:4]([C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH3:23])=[CH:18][C:17]=2[OH:24])=[C:11]([F:32])[CH:10]=1)[CH2:5][CH2:6][CH2:7][NH2:8])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 68547880N-acetyl-N1-[4-(2-Benzyloxy-4-ethylphenoxy)-3-fluorophenyl]propan-1,3-diamine

Product 1

HCID 68549004N-acetyl-N1-[4-(4-ethyl-2-hydroxyphenoxy)-3-fluorophenyl]propan-1,3-diamineYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

According to the procedure of example 20 (b) except substituting 4-ethyl-2-methoxy-1-[4-nitro-2-(trifluoromethyl) phenoxy]benzene for N-acetyl-N1-[4-(2-Benzyloxy-4-ethylphenoxy)-3-fluorophenyl]propan-1,3-diamine (70 mg, 0.16 mmol) and tetrahydrofurane for methanol (15 mL), the title compound (50 mg, 91%) was obtained as a brown liquid, after purification on silica gel (dichloromethane/ethyl acetate: 5/5)

Sources & evidence

ORD record
ord-8cbc1f9454ff44e4aeb5207f40b0b7d7
Source dataset
uspto-grants-2016_04
Patent number
US09309179B2

Reaction notes

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