Triethylamine → 2-(6-tert-Butyl-pyridin-3-yloxy)-N-(3-fluoro-4-methane sulfonylamino-benzyl)-acetamide

HRID 2265944Notes

Reaction equation

HRID 2265944 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH2:6][NH2:7].[C:16]([C:20]1[N:25]=[CH:24][C:23]([O:26][CH2:27][C:28](O)=[O:29])=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17].CCN(CC)CC>C1COCC1>[C:16]([C:20]1[N:25]=[CH:24][C:23]([O:26][CH2:27][C:28]([NH:7][CH2:6][C:5]2[CH:8]=[CH:9][C:10]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[C:3]([F:2])[CH:4]=2)=[O:29])=[CH:22][CH:21]=1)([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21097525N-[4-(aminomethyl)-2-fluorophenyl]methanesulfonamide hydrochlorideHCID 68786941(6-Tert-butyl-pyridin-3-yloxy)-acetic acid

Product 1

HCID 595982962-(6-tert-Butyl-pyridin-3-yloxy)-N-(3-fluoro-4-methane sulfonylamino-benzyl)-acetamideYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Fluoro-4-methanesulfonylaminobenzylamine hydrochloride (158 mg, 0.62 mmol) was reacted with (6-tert-butyl-pyridin-3-yloxy)-acetic acid (130 mg) DMTMM (1.2 eq, 206 mg) and NEt3(2.5 eq, 220 μl) in THF to give the title compound (165 mg, 65%) after purification by column chromatography (Hex/EtOAc=1/3).

Sources & evidence

ORD record
ord-c7f9340e73f643a69530fbfc68244673
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

Loading…