Triethylamine → 2-(4-tert-Butylphenoxy)-N-{3-methoxy-4-[(methysulfonyl)amino]benzyl}acetamide

HRID 1350835Notes

Reaction equation

HRID 1350835 reaction equation
FC(F)(F)[C:3](O)=[O:4].[NH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[CH:12][C:11]=1OC.[C:23]([C:27]1[CH:37]=[CH:36][C:30]([O:31][CH2:32][C:33]([OH:35])=O)=[CH:29][CH:28]=1)([CH3:26])([CH3:25])[CH3:24].Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.CN(C)C=O>[C:23]([C:27]1[CH:28]=[CH:29][C:30]([O:31][CH2:32][C:33]([NH:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([NH:16][S:17]([CH3:20])(=[O:18])=[O:19])=[C:14]([O:4][CH3:3])[CH:15]=2)=[O:35])=[CH:36][CH:37]=1)([CH3:24])([CH3:25])[CH3:26]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 157182-(4-Tert-butylphenoxy)acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69124640N-[4-(aminomethyl)-3-methoxyphenyl]methanesulfonamide trifluoroacetic acid

Product 1

HCID 210974722-(4-tert-Butylphenoxy)-N-{3-methoxy-4-[(methysulfonyl)amino]benzyl}acetamideYield 43%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of N-[4-(aminomethyl)-3-methoxyphenyl]methanesulfonamide trifluoroacetic acid (1.24 g, 3.6 mmol), (4-tert-butylphenoxy)acetic acid (625 mg, 3.0 mmol), 1-ethyl-3-(3′-dimethylaminopropyl) carbodiimide hydrogen chloride (EDC) (1.04 g, 5.4 mmol), triethylamine (1.21 g, 2.0 mmol) and 4-(dimethylamino)pyridine (DMAP) (110 mg, 0.9 mmol) in N,N-dimethylformamide (DMF) (30 ml) was treated in the same procedure described in Example 2(b) to give 543 mg (43% yield) of the title compound as a white amorphous solid.

Workup

  1. additionwas treated in the same procedure

Sources & evidence

ORD record
ord-09dd6a12c82847188d02a916c8bfa364
Source dataset
uspto-grants-2007_05
Patent number
US07214824B2

Reaction notes

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