Triphenylphosphine → (2S,3S)-tert-butyl 3-(tert-butyldimethylsilyloxy)-2-((6-((3-ethyl-4-(imidazo[1,2-a]pyridine-3-carboxamido)-1H-indazol-1-yl)methyl)pyridin-2-yloxy)methyl)pyrrolidine-1-carboxylate

HRID 79336

반응식

HRID 79336 반응식
[CH2:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH:12][C:13]([C:15]2[N:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]3=[N:17][CH:16]=2)=[O:14])[N:5]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[N:26]=2)[N:4]=1)[CH3:2].[Si:32]([O:39][C@H:40]1[CH2:44][CH2:43][N:42]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[C@H:41]1[CH2:52]O)([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Si:32]([O:39][C@H:40]1[CH2:44][CH2:43][N:42]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[C@H:41]1[CH2:52][O:31][C:27]1[CH:28]=[CH:29][CH:30]=[C:25]([CH2:24][N:5]2[C:6]3[C:11](=[C:10]([NH:12][C:13]([C:15]4[N:19]5[CH:20]=[CH:21][CH:22]=[CH:23][C:18]5=[N:17][CH:16]=4)=[O:14])[CH:9]=[CH:8][CH:7]=3)[C:3]([CH2:1][CH3:2])=[N:4]2)[N:26]=1)([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33]

참가 물질

7

반응물 5

HCID 11776TriphenylphosphineHCID 13097Triphenylphosphine OxideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 15921663(2S,3S)-tert-butyl 3-(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylateHCID 178437935HCID 178437935, 화합물

생성물 1

HCID 70815083(2S,3S)-tert-butyl 3-(tert-butyldimethylsilyloxy)-2-((6-((3-ethyl-4-(imidazo[1,2-a]pyridine-3-carboxamido)-1H-indazol-1-yl)methyl)pyridin-2-yloxy)methyl)pyrrolidine-1-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a suspension of N-(3-ethyl-1-((6-hydroxypyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (26 mg, 0.0630 mmol; prepared as in Example 17, Step A) in THF (5 mL) was added (2S,3S)-tert-butyl 3-(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate (62.7 mg, 0.189 mmol), triphenylphosphine (54.6 mg, 0.208 mmol) and diethyl azodicarboxylate (81.9 μL, 0.208 mmol). The suspension became a clear solution, which was stirred for 16 hours. The reaction mixture was concentrated under reduced pressure and silica gel chromatography (DCM/MeOH 10:1) provided the product mixed with triphenyl phosphine oxide (65.6 mg).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure and silica gel chromatography (DCM/MeOH 10:1)
  2. customprovided the product

출처 및 근거

ORD 기록
ord-d1f7ecc18de249d188a7702196579a7e
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841455B2

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