Diisopropylethylamine → 3,5-Dimethyl-isoxazole-4-sulphonic acid (4-[(4'-difluoromethoxy-biphenyl-4-ylamino)-methyl]-5-methyl-furan-2-carbonyl)-amide

HRID 460111Notes

Reaction equation

HRID 460111 reaction equation
C(N(C(C)C)CC)(C)C.[F:10][CH:11]([F:36])[O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([NH:25][CH2:26][C:27]3[CH:28]=[C:29]([C:33](O)=[O:34])[O:30][C:31]=3[CH3:32])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1.[CH3:37][C:38]1[C:42]([S:43]([NH2:46])(=[O:45])=[O:44])=[C:41]([CH3:47])[O:40][N:39]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O>[F:10][CH:11]([F:36])[O:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:20]=[CH:21][C:22]([NH:25][CH2:26][C:27]3[CH:28]=[C:29]([C:33]([NH:46][S:43]([C:42]4[C:38]([CH3:37])=[N:39][O:40][C:41]=4[CH3:47])(=[O:44])=[O:45])=[O:34])[O:30][C:31]=3[CH3:32])=[CH:23][CH:24]=2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 49623033,5-Dimethylisoxazole-4-sulfonamideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 184445644-(4'-Difluoromethoxy-biphenyl-4-ylaminomethyl)-5-methyl-furan-2-carboxylic acid

Product 1

HCID 588241993,5-Dimethyl-isoxazole-4-sulphonic acid (4-[(4'-difluoromethoxy-biphenyl-4-ylamino)-methyl]-5-methyl-furan-2-carbonyl)-amideYield 3.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Diisopropylethylamine (60 μl, 0.339 mmoles) and a solution of 4-(4′-difluoromethoxy-biphenyl-4-ylaminomethyl)-5-methyl-furan-2-carboxylic acid (171) (50 mg, 0.103 mmoles) in N,N-dimethylformamide (1.0 ml) were added to a stirred solution of 3,5-dimethyl-isoxazole-4-sulphonic acid amide (55 mg, 0.308 mmoles) in N,N-dimethylformamide (5.0 ml). A solution of O—(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (46 mg, 0.124 mmoles) in N,N-dimethylformamide (1.0 ml) was added and the mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated in vacuo and the residue was purified by HPLC to afford compound 174(2 mg) as a solid. LC/MS System D; Rt=10.35 mins, m/z (ES+)=532 (M+H for C25H23F2N3O6S).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-342d90e5462a4b399e9e214a6ec89a65
Source dataset
uspto-grants-2007_03
Patent number
US07196089B2

Reaction notes

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