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

反応式

HRID 590885 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a1a7e7a2af0941cfbae85fcd17e75210
出典データセット
uspto-grants-2016_01
特許番号
US09233979B2

関連ノート

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