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

HRID 1272879노트

반응식

HRID 1272879 반응식
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

참가 물질

6

반응물 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

생성물 1

HCID 11291651n-[4-(5-(1h-1,2,4-Triazol-5-yl)(1h-indazol-3-yl))phenyl]-2-furyl carboxamide수율 5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-a9c8910d4f014463b40cf99853af8705
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07208513B2

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