4-Methylmorpholine → 6-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)-N'-formylpyridazine-3-carbohydrazide

HRID 46199

反応式

HRID 46199 の反応式
[Cl:1][C:2]1[CH:17]=[CH:16][C:15]([C@H:18]2[C@H:23]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C@@H:22]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C@H:21]([O:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C@@H:20]([CH2:48][O:49][CH2:50][C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[O:19]2)=[CH:14][C:3]=1[CH2:4][C:5]1[N:10]=[N:9][C:8](C(O)=O)=[CH:7][CH:6]=1.[CH:57]([NH:59][NH2:60])=[O:58].CCN=C=NCCCN(C)C.O.ON1C2C=CC=CC=2N=N1.CN1CC[O:87][CH2:86]C1>CN(C)C=O>[Cl:1][C:2]1[CH:17]=[CH:16][C:15]([C@H:18]2[C@H:23]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C@@H:22]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C@H:21]([O:40][CH2:41][C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)[C@@H:20]([CH2:48][O:49][CH2:50][C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=3)[O:19]2)=[CH:14][C:3]=1[CH2:4][C:5]1[N:10]=[N:9][C:8]([C:57]([NH:59][NH:60][CH:86]=[O:87])=[O:58])=[CH:7][CH:6]=1

参加物

7

反応物 5

HCID 79724-MethylmorpholineHCID 12229HydrazinecarboxaldehydeHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 672878076-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)pyridazine-3-carboxylic acid

生成物 1

HCID 672870976-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)-N'-formylpyridazine-3-carbohydrazide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of 6-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)pyridazine-3-carboxylic acid (1.4 mmol) from Step 1, formic hydrazide (107 mg, 1.8 mmol), EDCI (394 mg, 2.1 mmol), and 1-hydroxybenzotriazole hydrate (426 mg, 2.7 mmol) in N,N-dimethylformamide (15 mL) was added 4-methylmorpholine (0.45 mL, 4.1 mmol). The resulting mixture was stirred at ambient temperature overnight. After dilution with ethyl acetate, the organic layer was subsequently washed with water, hydrochloric acid (1.0 M), saturated sodium bicarbonate and brine prior to drying over magnesium sulfate. Filtration and removal of the volatiles under reduced pressure yielded titled compound as a glassy off-white amorphous solid, which was used without further purification.

後処理

  1. washAfter dilution with ethyl acetate, the organic layer was subsequently washed with water, hydrochloric acid (1.0 M), saturated sodium bicarbonate and brine
  2. dry with materialto drying over magnesium sulfate
  3. filtrationFiltration and removal of the volatiles under reduced pressure

出典と根拠

ORDレコード
ord-b5ff48d00fc64eb9859cf9f69c2f2f6e
出典データセット
uspto-grants-2013_09
特許番号
US08541380B2

関連ノート

読み込み中…