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Hydrochloric Acid → HCID 20789121, 화합물

HRID 1272881
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HRID 1272881 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:41]=[C:42]([C:46]([NH:48][CH2:49][C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)=[O:47])[CH:43]=[CH:44][CH:45]=2)=[N:8]1.Cl.[OH-].[Na+]>O1CCOCC1>[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:41]=[C:42]([C:46]([NH:48][CH2:49][C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)=[O:47])[CH:43]=[CH:44][CH:45]=2)=[N:20][CH:19]=[N:18]1
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참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131724913HCID 131724913, 화합물

생성물 1

HCID 20789121HCID 20789121, 화합물수율 18.1%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
50 °C

실험 절차

To a stirred solution of (3-{1-perhydro-2H-pyran-2-yl-5-[1-(triphenylmethyl)(1,2,4-triazol-3-yl)](1H-indazol-3-yl)}phenyl)-N-benzylcarboxamide (0.232 g, 0.322 mmol) was added dioxane (10.0 mL) and aqueous 6 N hydrochloric acid (10.0 mL) and the mixture heated at 50° C. for 24 h. The mixture was cooled and aqueous 6 N sodium hydroxide (20 mL). Neutralization of the aqueous layer to pH=7 with aqueous 6 N hydrochloric acid followed by extraction with ethyl acetate, drying of the organic extracts over anhydrous sodium sulfate, filtration and evaporation gave crude product. Purification by preparative HPLC (15–80% acetonitrile/water) followed by washing with saturated sodium bicarbonate and extraction with ethyl acetate gave the title compound (0.0230 g, 18% yield). 1H NMR (CD3OD) δ 8.78 (s, 1H), 8.49 (t, 1H), 8.21 (dt, 1H), 8.11 (br d, 1H), 7.93 (dt, 1H), 7.69 (t, 1H), 7.65 (d, 1H), 7.40 (dd, 2H), 7.32 (m, 2H), 7.24 (m, 1H), 4.64 (s, 2H). ES-MS (m/z) 395 [M+1]+.

후처리

  1. temperatureThe mixture was cooled
  2. extractionNeutralization of the aqueous layer to pH=7 with aqueous 6 N hydrochloric acid followed by extraction with ethyl acetate
  3. dry with materialdrying of the organic extracts over anhydrous sodium sulfate, filtration and evaporation
  4. customgave crude product
  5. customPurification by preparative HPLC (15–80% acetonitrile/water)
  6. washby washing with saturated sodium bicarbonate and extraction with ethyl acetate

출처 및 근거

ORD 기록
ord-9d54633c9bfc444c9da488d5aebbd026
출처 데이터셋
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07208513B2

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