Ammonia → 2,5-difluoro-4-[2-pyridazin-4-yl-4-(trifluoromethyl)phenoxy]-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

HRID 1692216

反応式

HRID 1692216 の反応式
COC1C=C(OC)C=CC=1C[N:6]([C:19]1[S:23][N:22]=[CH:21][N:20]=1)[S:7]([C:10]1[CH:15]=[C:14]([F:16])[C:13](F)=[CH:12][C:11]=1[F:18])(=[O:9])=[O:8].[N:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:41]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:39]=[CH:38][C:37]=2[OH:46])=[CH:32][N:31]=1.C(=O)([O-])[O-].[K+].[K+].Cl.FC(F)(F)C(O)=O.N>CN(C)C=O.ClCCl.CO>[F:18][C:11]1[CH:12]=[C:13]([O:46][C:37]2[CH:38]=[CH:39][C:40]([C:42]([F:43])([F:44])[F:45])=[CH:41][C:36]=2[C:33]2[CH:34]=[CH:35][N:30]=[N:31][CH:32]=2)[C:14]([F:16])=[CH:15][C:10]=1[S:7]([NH:6][C:19]1[S:23][N:22]=[CH:21][N:20]=1)(=[O:8])=[O:9]

参加物

10

反応物 6

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 59436583N-(2,4-Dimethoxybenzyl)-2,4,5-trifluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamideHCID 1357416972-(Pyridazin-4-yl)-4-(trifluoromethyl)phenol

生成物 1

HCID 468413512,5-difluoro-4-[2-pyridazin-4-yl-4-(trifluoromethyl)phenoxy]-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

試薬・触媒・溶媒 3

HCID 887Methanol溶媒4 回HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒3 回

実験手順

The mixture of N-(2,4-dimethoxybenzyl)-2,4,5-trifluoro-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide (Preparation 647, 44 mg, 0.10 mmol), 2-pyridazin-4-yl-4-(trifluoromethyl)phenol (Preparation 712, 34 mg, 0.10 mmol), and potassium carbonate (55 mg, 0.40 mmol) in N,N-dimethylformamide (1.0 ml) was stirred at room temperature for 24 hours. The reaction mixture was poured into aqueous 2 M hydrochloric acid solution (5.0 ml) and filtered to give a solid. The solid was dissolved in dichloromethane (1.0 ml) and trifluoroacetic acid (1.0 ml) was added to the solution. The resulting solution was stirred for 16 hours. Methanol (5.0 ml) was added to the reaction mixture and filtered off polymeric solid. The filtrate was concentrated in vacuo to give a residue. The residue was passed through a 5 g SCX™ column with 1:1 dichloromethane:methanol solution and then 1:0.75:0.25 dichloromethane:methanol:7N ammonia solution in methanol. The filtrate was concentrated in vacuo and purified by HPLC. Yield 7.3 mg, 14%.

後処理

  1. filtrationfiltered
  2. customto give a solid
  3. stirringThe resulting solution was stirred for 16 hours
  4. filtrationfiltered off polymeric solid
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto give a residue
  7. concentrationThe filtrate was concentrated in vacuo
  8. custompurified by HPLC

出典と根拠

ORDレコード
ord-e78a27e210c24548a8e85b9ef76c3100
出典データセット
uspto-grants-2012_04
特許番号
US08153814B2

関連ノート

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