N-methyl-2-pyrrolidone → 2-(6-tert-Butyl-pyridin-3-yloxy)-N-(3-ethynyl-5-fluoro-4-methane sulfonylamino-benzyl)-acetamide

HRID 2265949Notes

Reaction equation

HRID 2265949 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:9]=[C:8]([F:10])[C:7]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[C:6]([C:16]#[CH:17])[CH:5]=1.[C:18]([C:22]1[N:27]=[CH:26][C:25]([O:28][CH2:29][C:30](O)=[O:31])=[CH:24][CH:23]=1)([CH3:21])([CH3:20])[CH3:19].CN1C(=O)CCC1>C1COCC1>[C:18]([C:22]1[N:27]=[CH:26][C:25]([O:28][CH2:29][C:30]([NH:2][CH2:3][C:4]2[CH:9]=[C:8]([F:10])[C:7]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[C:6]([C:16]#[CH:17])[CH:5]=2)=[O:31])=[CH:24][CH:23]=1)([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 68786941(6-Tert-butyl-pyridin-3-yloxy)-acetic acidHCID 866255193-Ethynyl-5-fluoro-4-methansulfonylaminobenzylamine hydrochloride

Product 1

HCID 595981352-(6-tert-Butyl-pyridin-3-yloxy)-N-(3-ethynyl-5-fluoro-4-methane sulfonylamino-benzyl)-acetamideYield 33.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(4-Aminomethyl-2-ethynyl-6-fluoro-phenyl)-methanesulfonamide HCl salt (120 mg, 0.43 mmol) was reacted with (6-tert-butyl-pyridin-3-yloxy)-acetic acid (90 mg) DMTMM (1.1 eq, 131 mg) and NMP (1.2 eq, 60 μl) in THF to give the title compound (62 mg, 33.3%) after purification by column chromatography (Hex EtOAc=2/3).

Sources & evidence

ORD record
ord-ab28b9c05fee4e9f89b427702d25114b
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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