Triethylamine → 2-(4-tert-Butyl-2-chlorophenoxy)-N-{3-fluoro-4-[(methylsulfonyl)amino]benzyl}acetamide

HRID 1350828Notes

Reaction equation

HRID 1350828 reaction equation
[C:1]([C:5]1[CH:15]=[CH:14][C:8]([O:9][CH2:10][C:11]([OH:13])=O)=[C:7]([Cl:16])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl-].ClC1N(C)CC[NH+]1C.C(N(CC)CC)C.Cl.[NH2:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([NH:42][S:43]([CH3:46])(=[O:45])=[O:44])=[C:38]([F:47])[CH:37]=1>O1CCCC1>[C:1]([C:5]1[CH:15]=[CH:14][C:8]([O:9][CH2:10][C:11]([NH:34][CH2:35][C:36]2[CH:41]=[CH:40][C:39]([NH:42][S:43]([CH3:46])(=[O:45])=[O:44])=[C:38]([F:47])[CH:37]=2)=[O:13])=[C:7]([Cl:16])[CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 230818(4-Tert-butyl-2-chlorophenoxy)acetic acidHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 21097525N-[4-(aminomethyl)-2-fluorophenyl]methanesulfonamide hydrochloride

Product 1

HCID 210974542-(4-tert-Butyl-2-chlorophenoxy)-N-{3-fluoro-4-[(methylsulfonyl)amino]benzyl}acetamideYield 7.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (4-tert-butyl-2-chlorophenoxy)acetic acid (121 mg, 0.5 mmol), 2-chloro-1,3-dimethylimidazolinium chloride (CDI) (90 mg, 0.55 mmol), triethylamine (0.30 ml), tetrahydrofuran (3.0 ml) and N-[4-(aminomethyl)-2-fluorophenyl]methanesulfonamide hydrochloride (127 mg, 0.5 mmol) was treated in the same procedure described in Example 2(b) to give 16 mg (7% yield) of the title compound as a white solid.

Workup

  1. additionwas treated in the same procedure

Sources & evidence

ORD record
ord-16c66ffa79e64cc0ba81ee536f0ca01b
Source dataset
uspto-grants-2007_05
Patent number
US07214824B2

Reaction notes

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