Diisopropylethylamine → tert-butyl 3-phenyl-5-(3-(pyridin-4-yl)-1-trityl-1H-indazol-5-ylcarbamoyl)piperidine-1-carboxylate

HRID 1467324노트

반응식

HRID 1467324 반응식
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[C:25]([O:29][C:30]([N:32]1[CH2:37][CH:36]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:35][CH:34]([C:44](O)=[O:45])[CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26].[N:47]1[CH:52]=[CH:51][C:50]([C:53]2[C:61]3[C:56](=[CH:57][CH:58]=[C:59]([NH2:62])[CH:60]=3)[N:55]([C:63]([C:76]3[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=3)([C:70]3[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=3)[C:64]3[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=3)[N:54]=2)=[CH:49][CH:48]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[C:38]1([CH:36]2[CH2:35][CH:34]([C:44](=[O:45])[NH:62][C:59]3[CH:60]=[C:61]4[C:56](=[CH:57][CH:58]=3)[N:55]([C:63]([C:70]3[CH:71]=[CH:72][CH:73]=[CH:74][CH:75]=3)([C:76]3[CH:77]=[CH:78][CH:79]=[CH:80][CH:81]=3)[C:64]3[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=3)[N:54]=[C:53]4[C:50]3[CH:51]=[CH:52][N:47]=[CH:48][CH:49]=3)[CH2:33][N:32]([C:30]([O:29][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:31])[CH2:37]2)[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 447848161-(Tert-butoxycarbonyl)-5-phenylpiperidine-3-carboxylic acidHCID 576858103-(pyridin-4-yl)-1-trityl-1H-indazol-5-amine

생성물 1

HCID 66613498tert-butyl 3-phenyl-5-(3-(pyridin-4-yl)-1-trityl-1H-indazol-5-ylcarbamoyl)piperidine-1-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU) (49 mg, 0.129 mmol) was added to a suspension of 1-(tert-butoxycarbonyl)-5-phenylpiperidine-3-carboxylic acid (36 mg, 0.117 mmol) in DMF (0.5 mL) and was stirred at room temperature for 15 minutes. A solution of 3-(pyridin-4-yl)-1-trityl-1H-indazol-5-amine (0.117 mmol) in DMF (0.5 mL) was added to the reaction and followed by diisopropyl ethyl amine (DIEA) (0.1 mL). The mixture was stirred at room temperature for an additional 30 minutes. The reaction was quenched with water (5 mL) and extracted with ethyl acetate (3×10 mL). The extracts were combined, dried using anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude product was progressed to the next step without purification.

후처리

  1. stirringThe mixture was stirred at room temperature for an additional 30 minutes
  2. customThe reaction was quenched with water (5 mL)
  3. extractionextracted with ethyl acetate (3×10 mL)
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was progressed to the next step without purification

출처 및 근거

ORD 기록
ord-951012ffd2304684821eeab656397753
출처 데이터셋
uspto-grants-2015_04
특허 번호
US08999957B2

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