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

HRID 490413Notes

Reaction equation

HRID 490413 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 (11.0 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 (11.0 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-9113f680cfe240ba9d6d89a5f4c21c63
Source dataset
uspto-grants-2009_05
Patent number
US07528157B2

Reaction notes

Loading…