Triethylamine → 3-(6-Chloro-pyridin-3-yl)-N-(3-fluoro-4-methane sulfonylamino-benzyl)-acrylamide

HRID 2265936Notes

Reaction equation

HRID 2265936 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(N(CC)CC)C.[Cl:23][C:24]1[N:29]=[CH:28][C:27]([CH:30]=[CH:31][C:32](O)=[O:33])=[CH:26][CH:25]=1.C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>C1COCC1.CCOC(C)=O>[Cl:23][C:24]1[N:29]=[CH:28][C:27]([CH:30]=[CH:31][C:32]([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:33])=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 21097525N-[4-(aminomethyl)-2-fluorophenyl]methanesulfonamide hydrochlorideHCID 534250563-(6-Chloropyridin-3-yl)prop-2-enoic acid

Product 1

HCID 723356623-(6-Chloro-pyridin-3-yl)-N-(3-fluoro-4-methane sulfonylamino-benzyl)-acrylamideYield 96%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Fluoro-4-methanesulfonylaminobenzylamine hydrochloride (51 mg, 0.201 mmol) was suspended in THF and treated with triethylamine (23 mg, 0.22 mmol) and then the resulting mixture was stirred for 10 mins. 3-(6-chloro-pyridin-3-yl)-acrylic acid (37 mg, 0.201 mmol) was added to the reaction mixture followed by DMTMM (61 mg, 0.22 mmol) after 10 mins. The resulting mixture was stirred overnight at ambient temperature and then diluted with EtOAc. The resulting solution was washed successively with water, sat'd NaHCO3 (×2), brine, and then dried over anhyd. Na2SO4, filtered and concentrated under reduced pressure. The crude residue was column-chromatographed to yield the title compound (74 mg, 96%).

Workup

  1. stirringThe resulting mixture was stirred overnight at ambient temperature
  2. washThe resulting solution was washed successively with water, sat'd NaHCO3 (×2), brine
  3. customdried over anhyd
  4. filtrationNa2SO4, filtered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was column-chromatographed

Sources & evidence

ORD record
ord-ca373f953f734803a6b9322ee87447c3
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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