Tetrahydrofuran → HCID 178520293、化合物

HRID 1349881ノート

反応式

HRID 1349881 の反応式
O1CCCCC1[N:7]1[C:15]2[C:10](=[CH:11][C:12]([C:16]3[N:20]=[CH:19][N:18](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:17]=3)=[CH:13][CH:14]=2)[C:9]([C:40]2[CH:45]=[CH:44][C:43]([NH2:46])=[CH:42][CH:41]=2)=[N:8]1.Cl.[C:48](Cl)(=O)[C:49]1[CH:54]=[CH:53][CH:52]=[N:51][CH:50]=1.C(N(CC)CC)C.[O:64]1CCC[CH2:65]1>>[NH:18]1[CH:19]=[N:20][C:16]([C:12]2[CH:11]=[C:10]3[C:15](=[CH:14][CH:13]=2)[NH:7][N:8]=[C:9]3[C:40]2[CH:45]=[CH:44][C:43]([NH:46][C:65](=[O:64])[CH2:48][C:49]3[CH:50]=[N:51][CH:52]=[CH:53][CH:54]=3)=[CH:42][CH:41]=2)=[N:17]1

参加物

5

反応物 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 224801494-{1-Perhydro-2h-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)]1h-indazol-3-yl}phenylamine

生成物 1

HCID 178520293HCID 178520293、化合物収率 56%

実験手順

To a solution of 4-{1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)]-1H-indazol-3-yl}phenylamine (0.306 g, 0.51 mmol) in tetrahydrofuran (4.5 mL) was added nicotinoyl chloride hydrochloride (0.409 g, 0.79 mmol) and triethylamine (0.35 mL, 2.52 mmol). The reaction mixture was stirred overnight at room temperature, and quenched with methanol (0.20 mL). This mixture was washed with sodium bicarbonate (aqueous) and extracted with ethyl acetate (3×). The organic fractions were combined, dried with magnesium sulfate, filtered, and condensed resulting in a crude solid (0.346 g) that was used without further purification. This solid was dissolved in 6 N hydrochloride solution (aqueous) (5 mL) and 1,4-dioxane (5 mL) and allowed to stir at room temperature overnight. The reaction was quenched by adding the reaction mixture dropwise to a solution of sodium bicarbonate (saturated aqueous) to form a precipitate, which was filtered and dried in a vacuum oven overnight. (0.109 g, 56% yield): 1H NMR (DMSO-d6) δ 9.12 (d, 1H), 8.78 (dd, 1H), 8.72 (s, 1H), 8.34 (dt,1H), 8.29 (s, 1H), 8.04 (m, 5H), 7.68 (d, 1H), 7.60 (ddd, 1H); ES-MS (m/z) 382 [M+1]+.

後処理

  1. customquenched with methanol (0.20 mL)
  2. washThis mixture was washed with sodium bicarbonate (aqueous)
  3. extractionextracted with ethyl acetate (3×)
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. customcondensed

出典と根拠

ORDレコード
ord-c8e772faaef949b989f6c9202801983d
出典データセット
uspto-grants-2007_05
特許番号
US07211594B2

反応ノート

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