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

HRID 626071Notes

Reaction equation

HRID 626071 reaction equation
[CH3:1][S:2]([N:5]([C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH3:24])=[CH:19][C:18]=2[O:25]CC2C=CC=CC=2)=[C:12]([F:33])[CH:11]=1)[CH2:6][CH2:7][CH2:8][NH2:9])(=[O:4])=[O:3].O1CCCC1>CO>[CH3:1][S:2]([N:5]([C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH3:24])=[CH:19][C:18]=2[OH:25])=[C:12]([F:33])[CH:11]=1)[CH2:6][CH2:7][CH2:8][NH2:9])(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 68549012N-Methanesulfonyl-N1-[4-(2-benzyloxy-4-ethylphenoxy)-3-fluorophenyl]propan-1,3-diamine

Product 1

HCID 68550583N-methanesulfonyl-N1-[4-(4-ethyl-2-hydroxyphenoxy)-3-fluorophenyl]propan-1,3-diamineYield 68.8%

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-Methanesulfonyl-N1-[4-(2-benzyloxy-4-ethylphenoxy)-3-fluorophenyl]propan-1,3-diamine (90 mg, 0.19 mmol) and tetrahydrofurane for methanol (15 mL), the title compound (50 mg, 68%) was obtained as a brown liquid, after purification on silica gel (dichloromethane/ethyl acetate: 8/2)

Sources & evidence

ORD record
ord-bebafff9c0ce427f81c854ce35988f46
Source dataset
uspto-grants-2016_04
Patent number
US09309179B2

Reaction notes

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