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Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → N-{[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N'-{[3'-(4-piperidinylmethyl)-3-biphenylyl]methyl}pentanediamide

HRID 657420
ノート
印刷プレビュー

反応式

HRID 657420 の反応式
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:29][CH3:30])=[C:10]([CH2:19][NH:20][C:21](=[O:28])[CH2:22][CH2:23][CH2:24][C:25]([OH:27])=O)[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].[NH2:31][CH2:32][C:33]1[CH:34]=[C:35]([C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([CH2:45][CH:46]3[CH2:51][CH2:50][N:49](C(OC(C)(C)C)=O)[CH2:48][CH2:47]3)[CH:40]=2)[CH:36]=[CH:37][CH:38]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:29][CH3:30])=[C:10]([CH2:19][NH:20][C:21](=[O:28])[CH2:22][CH2:23][CH2:24][C:25]([NH:31][CH2:32][C:33]3[CH:34]=[C:35]([C:39]4[CH:44]=[CH:43][CH:42]=[C:41]([CH2:45][CH:46]5[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]5)[CH:40]=4)[CH:36]=[CH:37][CH:38]=3)=[O:27])[C:11]([NH:12][CH:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57813360tert-Butyl 4-{[3'-(aminomethyl)biphenyl-3-yl]methyl}piperidine-1-carboxylateHCID 578198975-({[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)-5-oxopentanoic Acid

生成物 1

HCID 44242619
N-{[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N'-{[3'-(4-piperidinylmethyl)-3-biphenylyl]methyl}pentanediamide
収率 35.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 5-({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)-5-oxopentanoic acid (0.0807 g, 0.200 mmol) in DCM (1 mL) was added 1,1-dimethylethyl 4-{[3′-(aminomethyl)-3-biphenylyl]methyl}-1-piperidinecarboxylate (0.0837 g, 0.220 mmol), HBTU (0.0910 g, 0.240 mmol), and TEA (0.0562 mL, 0.400 mmol), and was stirred at room temperature for 16 h. The reaction mixture was concentrated on a Glas-Col evaporator, purified using a Gilson HPLC and concentrated with Biotachi evaporator. The crude product was dissolved in DCM (0.6 mL), and TFA (0.2 mL) was added. The resultant mixture was left at room temperature for 1 h before being concentrated on a Glas-Col evaporator, purified using a Gilson HPLC (acidic conditions: with 0.1% TFA) and basified with an amine cartridge to afford the title compound 0.048 g (35%). LC-MS m/z 680.

後処理

  1. concentrationThe reaction mixture was concentrated on a Glas-Col evaporator
  2. custompurified
  3. concentrationconcentrated with Biotachi evaporator
  4. dissolutionThe crude product was dissolved in DCM (0.6 mL)
  5. additionTFA (0.2 mL) was added
  6. waitThe resultant mixture was left at room temperature for 1 h
  7. concentrationbefore being concentrated on a Glas-Col evaporator
  8. custompurified

出典と根拠

ORDレコード
ord-f5ef1342023d4f0e86607f50388b1f39
出典データセット
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08071588B2

反応ノート

読み込み中…

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