Hydrochloric Acid → 3-(4-tert-Butyl-phenyl)-N-(4-methanesulfonylamino-2-methoxy-5-vinyl-benzyl)-acrylamide

HRID 2358419Notes

Reaction equation

HRID 2358419 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[C:13]([CH:14]=[CH2:15])=[CH:12][C:9]([CH2:10][NH2:11])=[C:8]([O:16][CH3:17])[CH:7]=1)(=[O:4])=[O:3].Cl.FC(F)(F)C(O)=O.[C:26]([C:30]1[CH:35]=[CH:34][C:33]([CH:36]=[CH:37][C:38](O)=[O:39])=[CH:32][CH:31]=1)([CH3:29])([CH3:28])[CH3:27].C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>C(Cl)Cl.C(N(CC)CC)C>[C:26]([C:30]1[CH:31]=[CH:32][C:33]([CH:36]=[CH:37][C:38]([NH:11][CH2:10][C:9]2[CH:12]=[C:13]([CH:14]=[CH2:15])[C:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:7][C:8]=2[O:16][CH3:17])=[O:39])=[CH:34][CH:35]=1)([CH3:29])([CH3:27])[CH3:28]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 7248384-Tert-butylcinnamic acidHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 684562614-Methanesulfonylamino-2-methoxy-5-vinyl-benzylamine

Product 1

HCID 684560973-(4-tert-Butyl-phenyl)-N-(4-methanesulfonylamino-2-methoxy-5-vinyl-benzyl)-acrylamideYield 19%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a ice-cooled solution of 4-methanesulfonylamino-2-methoxy-5-vinyl-benzylamine and HCl salt (220 mg, 0.73 mmol) prepared in the synthesis of Example 48 in methylene chloride was treated with trifluoroacetic acid (100 mg, 0.88 mmol)) for 1 hr, and then concentrated under reduced pressure. The part of the crude residue (50 mg, 0.13 mmol) was suspended in methylene chloride and treated with triethylamine followed by 3-(4-tert-butyl-phenyl)-acrylic acid (30 mg) and DMTMM (40 mg). The resulting mixture was stirred for 2 days at ambient temperature and concentrated under reduced pressure. The crude residue was column-chromatographed (hexane/ethylacetate=3/2) to yield a white solid (11 mg, 19%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. concentrationconcentrated under reduced pressure
  3. customThe crude residue was column-chromatographed (hexane/ethylacetate=3/2)

Sources & evidence

ORD record
ord-b4088123dd1340a092b0bf9a3ac428e0
Source dataset
uspto-grants-2010_07
Patent number
US07763657B2

Reaction notes

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