4-Tert-butylcinnamic acid → 3-(4-t-Butyl-phenyl)-N-(2,5-difluoro-4-methanesulfonylamino-benzyl)-acrylamide

HRID 2423337Notes

Reaction equation

HRID 2423337 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[C:9]([F:10])=[CH:8][C:7]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[C:6]([F:16])[CH:5]=1.[C:17]([C:21]1[CH:26]=[CH:25][C:24]([CH:27]=[CH:28][C:29](O)=[O:30])=[CH:23][CH:22]=1)([CH3:20])([CH3:19])[CH3:18].C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>O1CCCC1>[C:17]([C:21]1[CH:22]=[CH:23][C:24]([CH:27]=[CH:28][C:29]([NH:2][CH2:3][C:4]2[CH:5]=[C:6]([F:16])[C:7]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[CH:8][C:9]=2[F:10])=[O:30])=[CH:25][CH:26]=1)([CH3:20])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 7248384-Tert-butylcinnamic acidHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 67241880N-(4-aminomethyl-2,5-difluoro-phenyl)-methanesulfonamide hydrochloride

Product 1

HCID 672425043-(4-t-Butyl-phenyl)-N-(2,5-difluoro-4-methanesulfonylamino-benzyl)-acrylamideYield 75.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the 25 ml round bottom flask were put N-(4-aminomethyl-2,5-difluoro-phenyl)-methanesulfonamide hydrochloride (125 mg, 0.46 mmol), 3-(4-t-butylphenyl)acrylic acid (1.2 eq, 112 mg), and DMTMM (1.2 eq, 152 mg). And to this mixture was poured 15 ml tetrahydrofuran and stirred 12 hours at room temperature. After confirming the completion of the reaction with TLC, the reaction mixture was extracted with ethylacetate, washed 1N HCl solution. And the combined organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The obtained liquid was purified with column chromatography (n-hexane/ethyl acetate=1/1) to yield a solid (147 mg).

Workup

  1. customthe completion of the reaction with TLC
  2. extractionthe reaction mixture was extracted with ethylacetate
  3. washwashed 1N HCl solution
  4. dry with materialAnd the combined organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained liquid was purified with column chromatography (n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-35cf7f92672740d3afa1c3115d8bb0b6
Source dataset
uspto-grants-2011_06
Patent number
US07960584B2

Reaction notes

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