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Triethylamine → N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N'-({3'-[(1-methyl-4-piperidinyl)methyl]-3-biphenylyl}methyl)-2,6-pyridinedicarboxamide

HRID 662127
ノート
印刷プレビュー

反応式

HRID 662127 の反応式
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:32][CH3:33])=[C:10]([CH2:19][NH:20][C:21]([C:23]3[N:28]=[C:27]([C:29]([OH:31])=O)[CH:26]=[CH:25][CH:24]=3)=[O:22])[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].[CH3:34][N:35]1[CH2:40][CH2:39][CH:38]([CH2:41][C:42]2[CH:43]=[C:44]([C:48]3[CH:53]=[CH:52][CH:51]=[C:50]([CH2:54][NH2:55])[CH:49]=3)[CH:45]=[CH:46][CH:47]=2)[CH2:37][CH2:36]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>CS(C)=O.C(Cl)Cl>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:32][CH3:33])=[C:10]([CH2:19][NH:20][C:21]([C:23]3[CH:24]=[CH:25][CH:26]=[C:27]([C:29]([NH:55][CH2:54][C:50]4[CH:49]=[C:48]([C:44]5[CH:45]=[CH:46][CH:47]=[C:42]([CH2:41][CH:38]6[CH2:39][CH2:40][N:35]([CH3:34])[CH2:36][CH2:37]6)[CH:43]=5)[CH:53]=[CH:52][CH:51]=4)=[O:31])[N:28]=3)=[O:22])[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

7

反応物 4

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57813254({3'-[(1-Methyl-4-piperidinyl)methyl]-3-biphenylyl}methyl)amineHCID 578193746-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]-2-pyridinecarboxylic acid

生成物 1

HCID 44193617
N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N'-({3'-[(1-methyl-4-piperidinyl)methyl]-3-biphenylyl}methyl)-2,6-pyridinedicarboxamide
収率 55.6%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 6344Dichloromethane溶媒

実験手順

Process (B) In an alternate preparation of the titled compound, to a solution of 6-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]-2-pyridinecarboxylic acid (45 mg, 0.1 mmol) in DMSO (1 mL) was added 1-{3′-[(1-methyl-4-piperidinyl)methyl]-3-biphenylyl}methanamine (28 mg, 0.095 mmol), HBTU (42 mg, 0.11 mmol) and Et3N (0.021 mL, 0.15 mmol) in DCM (3 mL). The resulting mixture was stirred at room temperature for 18 h. The reaction was quenched with H2O (2 drops), purified with a Gilson HPLC (with 0.1% TFA), concentrated, re-dissolved in EtOAc, washed with NaOH (1N), dried over Na2SO4, filtered, concentrated and dried with a high vacuum oil pump to afford the title compound as a white solid 38.5 mg (53%). LC-MS m/z 729 (M+H)+.

後処理

  1. customThe reaction was quenched with H2O (2 drops)
  2. custompurified with a Gilson HPLC (with 0.1% TFA)
  3. concentrationconcentrated
  4. dissolutionre-dissolved in EtOAc
  5. washwashed with NaOH (1N)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customdried with a high vacuum oil

出典と根拠

ORDレコード
ord-8bbb316d57604737bee1017f8eef5e1f
出典データセット
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08084449B2

反応ノート

読み込み中…

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