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4-Methylmorpholine → 5-(4-Chloro-phenyl)-6-(2,2,2-trifluoro-ethoxy)-pyridazine-3-carboxylic acid (5-cyclopropyl-[1,2,4]oxadiazol-3-ylmethyl)-amide

HRID 1528444
ノート
印刷プレビュー

反応式

HRID 1528444 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:20](O)=[O:21])[N:11]=[N:12][C:13]=2[O:14][CH2:15][C:16]([F:19])([F:18])[F:17])=[CH:4][CH:3]=1.CN1CCOCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[CH:55]1([C:58]2[O:62][N:61]=[C:60]([CH2:63][NH2:64])[N:59]=2)[CH2:57][CH2:56]1>CN(C)C=O>[CH:55]1([C:58]2[O:62][N:61]=[C:60]([CH2:63][NH:64][C:20]([C:10]3[N:11]=[N:12][C:13]([O:14][CH2:15][C:16]([F:17])([F:18])[F:19])=[C:8]([C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=4)[CH:9]=3)=[O:21])[N:59]=2)[CH2:57][CH2:56]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 79724-MethylmorpholineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 56773494(5-Cyclopropyl-1,2,4-oxadiazol-3-yl)methanamine hydrochlorideHCID 66678582HCID 66678582、化合物

生成物 1

HCID 569286935-(4-Chloro-phenyl)-6-(2,2,2-trifluoro-ethoxy)-pyridazine-3-carboxylic acid (5-cyclopropyl-[1,2,4]oxadiazol-3-ylmethyl)-amide
収率 66.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of 5-(4-chloro-phenyl)-6-(2,2,2-trifluoro-ethoxy)-pyridazine-3-carboxylic acid (example M, 100 mg, 0.300 mmol) in dimethylformamide (4 mL, dried), was added 4-methylmorpholine (CAS No. 109-02-4, 0.09 mL 0.901 mmol), HBTU (CAS No. 94790-37-1, 171 mg, 0.450 mmol), 5-cyclopropyl-[1,2,4]oxadiazol-3-methanamine hydrochloride (Chembridge, MFCD09864586, 52 mg, 0.300 mmol) at rt and this mixture was stirred for 12 h at rt. Volatile were removed under reduced pressure and the residue was extracted with ethyl acetate. The combined organic layer was washed with aq. NaHCO3 soln, brine and concentrated to afford the crude residue which was purified by column chromatography (100-200 silica gel, elution with ethyl acetate/hexane). The title compound (91 mg, 66.0% yield) was obtained as a white solid; LC-MS (UV peak area/ESI) 96.8%, 454.6 (M+H)+.

後処理

  1. customVolatile were removed under reduced pressure
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe combined organic layer was washed with aq. NaHCO3 soln
  4. concentrationbrine and concentrated
  5. customto afford the crude residue which
  6. customwas purified by column chromatography (100-200 silica gel, elution with ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-0da85fbeb6f34752badcdbe4f05f5c3e
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09090599B2

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート