Imidazole → Methyl (S)-2-(3-(3-(bis(4-methoxybenzyl)amino)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)ureido)-2-phenylacetate

HRID 590885

반응식

HRID 590885 반응식
[CH3:1][O:2][C:3]1[CH:48]=[CH:47][C:6]([CH2:7][N:8]([CH2:38][C:39]2[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=2)[C:9]2[C:13]3[CH:14]=[N:15][C:16]([NH2:18])=[CH:17][C:12]=3[N:11]([C:19]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:10]=2)=[CH:5][CH:4]=1.C1N=CN([C:54](N2C=NC=C2)=[O:55])C=1.N1C=CN=C1.CCN(C(C)C)C(C)C.[CH3:75][O:76][C:77](=[O:86])[C@@H:78]([NH2:85])[C:79]1[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=1>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]([CH2:38][C:39]2[CH:40]=[CH:41][C:42]([O:45][CH3:46])=[CH:43][CH:44]=2)[C:9]2[C:13]3[CH:14]=[N:15][C:16]([NH:18][C:54](=[O:55])[NH:85][C@@H:78]([C:79]4[CH:80]=[CH:81][CH:82]=[CH:83][CH:84]=4)[C:77]([O:76][CH3:75])=[O:86])=[CH:17][C:12]=3[N:11]([C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[N:10]=2)=[CH:47][CH:48]=1

참가 물질

7

반응물 5

HCID 795ImidazoleHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 1201451Methyl phenylglycinate, L-HCID 1182723773-N,N-bis(4-methoxybenzyl)-1-trityl-1H-pyrazolo[4,3-c]pyridine-3,6-diamine

생성물 1

HCID 131734504Methyl (S)-2-(3-(3-(bis(4-methoxybenzyl)amino)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)ureido)-2-phenylacetate

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To a solution of 3-N,N-bis(4-methoxybenzyl)-1-trityl-1H-pyrazolo[4,3-c]pyridine-3,6-diamine (0.1 g, 0.16 mmol) in anhydrous 1,4-dioxane (3 mL) was added CDI (0.13 g, 0.79 mmol) followed by the addition of imidazole (0.05 g, 0.78 mmol) and the contents were stirred at ambient temperature. After 16 h, DIPEA (0.12 mL, 0.64 mmol) and (S)-methyl-2-amino-2-phenylacetate (0.064 g, 0.32 mmol) were added and stirred. After 2 h, the reaction mixture was quenched with H2O and the organic contents were extracted with EtOAc (2×20 mL), dried over anhydrous Na2SO4 and concentrated. The residue thus obtained was purified by preparative HPLC to afford the title compound MS ES calc'd. for C51H46N6O5 [M+H]+ 823. Found 823.

후처리

  1. stirringstirred
  2. waitAfter 2 h
  3. customthe reaction mixture was quenched with H2O
  4. extractionthe organic contents were extracted with EtOAc (2×20 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customThe residue thus obtained
  8. customwas purified by preparative HPLC

출처 및 근거

ORD 기록
ord-a1a7e7a2af0941cfbae85fcd17e75210
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09233979B2

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