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

HRID 657298
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HRID 657298 반응식
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:27][CH3:28])=[C:10]([CH2:19][NH:20][C:21](=[O:26])[CH2:22][C:23]([OH:25])=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].[Br:29][C:30]1[CH:31]=[C:32]([CH2:38][NH2:39])[CH:33]=[CH:34][C:35]=1[O:36][CH3:37].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>ClCCl>[Br:29][C:30]1[CH:31]=[C:32]([CH2:38][NH:39][C:23](=[O:25])[CH2:22][C:21]([NH:20][CH2:19][C:10]2[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]3[CH:5]=[N:4][N:3]([CH2:1][CH3:2])[C:7]3=[N:8][C:9]=2[CH2:27][CH3:28])=[O:26])[CH:33]=[CH:34][C:35]=1[O:36][CH3:37]
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참가 물질

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반응물 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22026276(3-Bromo-4-methoxyphenyl)methanamineHCID 578198663-({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)-3-oxopropanoic acid

생성물 1

HCID 57819863
N-{[3-bromo-4-(methyloxy)phenyl]methyl}-N'-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}propanediamide
수율 88.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A mixture of 3-({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)-3-oxopropanoic acid (0.6 g, 1.541 mmol), 1-[3-bromo-4-(methyloxy)phenyl]methanamine (0.389 g, 1.8 mmol), HATU (0.760 g, 2.0 mmol), and triethylamine (0.599 ml, 4.3 mmol) in dichloromethane (40 mL) was stirred overnight at room temperature to give a pale yellow solution. The reaction mixture was diluted with DCM, washed with saturated NaHCO3 and then saturated NaCl. The organic layer was dried over Na2SO4, evaporated to dryness which gave viscous syrup. The viscous syrup was chromatographed on an 80 g Combi-Flash Column in silica with DCM-MeOH (0-8%). The product from this purification was placed on a Chromatotron Plate (2000μ) silica eluting with DCM-MeOH (3.5%) to give N-{[3-bromo-4-(methyloxy)phenyl]methyl}-N′-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}propanediamide (800 mg, 88%). LC-MS m/z 587.3 (M+H)+, 0.83 min (ret time).

후처리

  1. customto give a pale yellow solution
  2. washwashed with saturated NaHCO3
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customevaporated to dryness which
  5. customgave viscous syrup
  6. customThe viscous syrup was chromatographed on an 80 g Combi-Flash Column in silica with DCM-MeOH (0-8%)
  7. customThe product from this purification

출처 및 근거

ORD 기록
ord-eb1438cc30714319a4d57139329959f0
출처 데이터셋
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08071588B2

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