Lithium Hexamethyldisilazide → 7-chloro-N-(1-((1-isopropyl-1H-pyrazol-3-yl)methyl)-3-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 706590노트

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HRID 706590 반응식
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[NH2:11])[N:4]([CH2:12][C:13]2[CH:17]=[CH:16][N:15]([CH:18]([CH3:20])[CH3:19])[N:14]=2)[N:3]=1.[Cl:21][C:22]1[CH:27]=[CH:26][N:25]2[C:28]([C:31](OCC)=[O:32])=[CH:29][N:30]=[C:24]2[CH:23]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1>[Cl:21][C:22]1[CH:27]=[CH:26][N:25]2[C:28]([C:31]([NH:11][C:9]3[CH:8]=[CH:7][CH:6]=[C:5]4[C:10]=3[C:2]([CH3:1])=[N:3][N:4]4[CH2:12][C:13]3[CH:17]=[CH:16][N:15]([CH:18]([CH3:20])[CH3:19])[N:14]=3)=[O:32])=[CH:29][N:30]=[C:24]2[CH:23]=1

참가 물질

5

반응물 3

HCID 2733832Lithium HexamethyldisilazideHCID 67107280Ethyl 7-chloroimidazo[1,2-A]pyridine-3-carboxylateHCID 866993293-Methyl-1-((1-isopropylpyrazole-3-yl)methyl)-4-amino-1H-indazole

생성물 1

HCID 679740927-chloro-N-(1-((1-isopropyl-1H-pyrazol-3-yl)methyl)-3-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide수율 52%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

3-Methyl-1-((1-isopropylpyrazole-3-yl)methyl)-4-amino-1H-indazole (1 equivalent) and ethyl 7-chloroimidazo[1,2-a]pyridine-3-carboxylate (Example 7 step D; 1 equivalent) were dissolved in dry THF (0.2 M) and the resulting solution was cooled to 0° C. Lithium bis(trimethylsilyl)amide (2.3 equivalents) was slowly added and the resulting mixture was allowed to warm to ambient temperature overnight. THF was removed under vacuum and the remaining material was partitioned between water and ethyl acetate. The bottom aqueous layer was extracted twice with ethyl acetate. The combined organic extracts were combined, dried over sodium sulfate, filtered and \ concentrated to give desired compound (52% yield).

후처리

  1. temperatureto warm to ambient temperature overnight
  2. customTHF was removed under vacuum
  3. customthe remaining material was partitioned between water and ethyl acetate
  4. extractionThe bottom aqueous layer was extracted twice with ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentration\ concentrated

출처 및 근거

ORD 기록
ord-2f49b428d034488fab4c6531f458e028
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174981B2

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