Tetrahydrofuran → HCID 67244353, compound

HRID 2423344Notes

Reaction equation

HRID 2423344 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[C:6]([F:15])[CH:5]=1.[C:16]([C:20]1[CH:25]=[CH:24][C:23]([C:26]([CH3:31])=[CH:27][C:28](O)=[O:29])=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17].C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-].O1CCCC1>C(N(CC)CC)C>[F:15][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[NH:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH2:3][NH:2][C:28](=[O:29])[CH:27]=[C:26]([C:23]1[CH:22]=[CH:21][C:20]([C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:25][CH:24]=1)[CH3:31]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 21097525N-[4-(aminomethyl)-2-fluorophenyl]methanesulfonamide hydrochlorideHCID 67244312HCID 67244312, compound

Product 1

HCID 67244353HCID 67244353, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To the 50 ml of round bottom flask were put N-(4-aminomethyl-2-fluoro-phenyl)-methanesulfonamide hydrochloride (0.14 g, 0.55 mmol), 3-(4-t-butylphenyl)-but-2-enoic acid (1.0 eq, 0.12 g) and DMTMM (1.2 eq, 0.183 g). To this mixture was poured 25 ml tetrahydrofuran, added triethylamine (excess, 0.5 ml) 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. 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 the title compound (41.5 mg)

Workup

  1. customTo the 50 ml of round bottom flask were put
  2. customthe completion of the reaction with TLC
  3. extractionthe reaction mixture was extracted with ethylacetate
  4. washwashed 1N HCl solution
  5. dry with materialThe combined organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained liquid was purified with column chromatography (n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-f5528a5cb6a64b61b0a6aac44182f247
Source dataset
uspto-grants-2011_06
Patent number
US07960584B2

Reaction notes

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