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Sodium Carbonate → Tert-butyl 3-(4-chlorobenzyl)-4-(4-(3-methyl-5-phenyl-1h-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-4-oxobutylcarbamate

HRID 79560
ノート
印刷プレビュー

反応式

HRID 79560 の反応式
[CH3:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:9]=2[N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[NH:4][CH:3]=1.[C:23]([O:27][C:28]([NH:30][CH2:31][CH2:32][CH:33]([CH2:37][C:38]1[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][CH:39]=1)[C:34](O)=[O:35])=[O:29])([CH3:26])([CH3:25])[CH3:24].C1C=CC2N(O)N=NC=2C=1.O.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Cl:44][C:41]1[CH:42]=[CH:43][C:38]([CH2:37][CH:33]([C:34]([N:14]2[CH2:13][CH2:12][N:11]([C:9]3[C:8]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)=[CH:7][N:6]=[C:5]4[NH:4][CH:3]=[C:2]([CH3:1])[C:10]=34)[CH2:16][CH2:15]2)=[O:35])[CH2:32][CH2:31][NH:30][C:28](=[O:29])[O:27][C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:39][CH:40]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 6

HCID 10340Sodium CarbonateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 687376094-(Tert-butoxycarbonylamino)-2-(4-chlorobenzyl)butanoic acidHCID 687614063-Methyl-5-phenyl-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine

生成物

1
HCID 68758679Tert-butyl 3-(4-chlorobenzyl)-4-(4-(3-methyl-5-phenyl-1h-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-4-oxobutylcarbamate収率 12.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

3-Methyl-5-phenyl-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine (0.050 g, 0.137 mmol, see Example 15), 4-(tert-butoxycarbonylamino)-2-(4-chlorobenzyl)butanoic acid (0.0494 g, 0.151 mmol), HOBT-H2O (0.0293 g, 0.192 mmol), and EDCI (0.0341 g, 0.178 mmol) were placed in DCM (3 mL) at room temperature. DIEA (d=0.742; 0.119 mL, 0.684 mmol) was then added, and the reaction was stirred at room temperature for 15 hours. The reaction was then poured into saturated Na2CO3 and extracted with DCM. The combined organic fractions were dried, filtered, concentrated, and purified (500:5 DCM:MeOH) to give tert-butyl 3-(4-chlorobenzyl)-4-(4-(3-methyl-5-phenyl-1H-pyrrolo[2,3-b]pyri din-4-yl)piperazin-1-yl)-4-oxobutylcarbamate (0.010 g, 12.1% yield).

後処理

  1. extractionextracted with DCM
  2. customThe combined organic fractions were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified (500:5 DCM:MeOH)

出典と根拠

ORDレコード
ord-b96e1c83c2d44f9580512575df724249
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08841304B2

反応ノート

読み込み中…

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