N-methyl-2-pyrrolidone → 3-(2-Bromo-6-tert-butyl-pyridin-3-yl)-N-(3-ethynyl-5-fluoro-4-methanesulfonylamino-benzyl)-acrylamide

HRID 2265954Notes

Reaction equation

HRID 2265954 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.[Br:18][C:19]1[C:24]([CH:25]=[CH:26][C:27](O)=[O:28])=[CH:23][CH:22]=[C:21]([C:30]([CH3:33])([CH3:32])[CH3:31])[N:20]=1.C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-].CN1C(=O)CCC1>C1COCC1>[Br:18][C:19]1[C:24]([CH:25]=[CH:26][C:27]([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:28])=[CH:23][CH:22]=[C:21]([C:30]([CH3:33])([CH3:32])[CH3:31])[N:20]=1

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 866255193-Ethynyl-5-fluoro-4-methansulfonylaminobenzylamine hydrochlorideHCID 866255233-(2-Bromo-6-tert-butyl-pyridin-3-yl)-acrylic acid

Product 1

HCID 743323913-(2-Bromo-6-tert-butyl-pyridin-3-yl)-N-(3-ethynyl-5-fluoro-4-methanesulfonylamino-benzyl)-acrylamideYield 55.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(4-Aminomethyl-2-ethynyl-6-fluoro-phenyl)-methanesulfonamide HCl salt (41.2 mg, 0.148 mmol) was reacted with 3-(2-bromo-6-tert-butyl-pyridin-3-yl)-acrylic acid (1.0 eq, 42 mg), DMTMM (1.0 eq, 41 mg) and NMP (1.2 eq, 20 μl) in THF to give the title compound (42 mg, 55.8%) after purification by column chromatography (Hex/EtOAc=3/2).

Sources & evidence

ORD record
ord-7555bd7d430e4e068f2850dddc862fe0
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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