Triethylamine → n-[4-(5-(1h-1,2,4-Triazol-5-yl)(1h-indazol-3-yl))phenyl]-2-furyl carboxamide

HRID 1349734ノート

反応式

HRID 1349734 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.C(N(CC)CC)C.[O:54]1[CH:58]=[CH:57][CH:56]=[C:55]1[C:59](Cl)=[O:60].C(=O)(O)[O-].[Na+]>O1CCCC1>[NH:17]1[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:59]([C:55]3[O:54][CH:58]=[CH:57][CH:56]=3)=[O:60])=[CH:42][CH:41]=2)=[N:20][CH:19]=[N:18]1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 516892Sodium BicarbonateHCID 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 11291651n-[4-(5-(1h-1,2,4-Triazol-5-yl)(1h-indazol-3-yl))phenyl]-2-furyl carboxamide収率 5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

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 (0.300 g, 0.498 mmol) was added tetrahydrofuran (4.50 mL), triethylamine (0.345 mL, 2.48 mmol), and 2-furoyl chloride (0.058 mL, 0.735 mmol). The mixture was stirred for 16 h at ambient temperature and poured into saturated sodium bicarbonate (50 mL). The aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with saturated sodium bicarbonate, dried over anhydrous sodium sulfate, filtered and evaporated. Purification by preparative HPLC (30–80% acetonitrile/water) followed by washing with saturated sodium bicarbonate and extraction with ethyl acetate gave the title compound (0.0086 g, 5% yield). 1H NMR (DMSO-d6) δ 8.75 (d, 1H), 8.10 (m, 6H), 7.74 (m, 1H), 7.39 (d, 1H), 6.75 (m, 1H). ES-MS (m/z) 371 [M+1]+

後処理

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. washThe combined organic extracts were washed with saturated sodium bicarbonate
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by preparative HPLC (30–80% acetonitrile/water)
  7. washby washing with saturated sodium bicarbonate and extraction with ethyl acetate

出典と根拠

ORDレコード
ord-8d5c205a1786425b89e053974b3eb2c2
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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