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

HRID 564534ノート

反応式

HRID 564534 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[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=3)[C:26]([OH:28])=O)=[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].[Br:34][C:35]1[CH:36]=[C:37]([CH2:43]N)[CH:38]=[C:39]([O:41][CH3:42])[CH:40]=1.C[N:46](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>C(Cl)Cl>[Br:34][C:35]1[CH:36]=[C:37]([CH2:43][N: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[CH2:32][CH3:33])[C:21]([C:23]2[CH:31]=[CH:30][CH:29]=[C:25]([C:26]([NH2:46])=[O:28])[CH:24]=2)=[O:22])[CH:38]=[C:39]([O:41][CH3:42])[CH:40]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 534144413-Bromo-5-methoxybenzenemethanamineHCID 578132773-[({[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoic Acid

生成物 1

HCID 67006812N-{[3-bromo-5-(methyloxy)phenyl]methyl}-N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-1,3-benzenedicarboxamide収率 96%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoic acid (762 mg, 1.69 mmol), {[3-bromo-5-(methyloxy)phenyl]methyl}amine (529 mg, 1.86 mmol), HBTU (769 mg, 2.03 mmol) and Et3N (0.47 mL, 3.38 mmol) in DCM was stirred at room temperature overnight. The reaction was quenched with saturated NaHCO3 and extracted with DCM twice. The combined organic layers were then washed with water followed by a brine wash. The organic layer was then concentrated under vacuum to give a crude residue. It was then purified using CombiFlash chromatography eluting with 0 to 10% methanol in DCM to obtain N-{[3-bromo-5-(methyloxy)phenyl]methyl}-N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-1,3-benzenedicarboxamide as a solid (1.05 g, 96%). LC-MS m/z 649 (M+H)+.

後処理

  1. customThe reaction was quenched with saturated NaHCO3
  2. extractionextracted with DCM twice
  3. washThe combined organic layers were then washed with water
  4. washwash
  5. concentrationThe organic layer was then concentrated under vacuum
  6. customto give a crude residue
  7. customIt was then purified
  8. washeluting with 0 to 10% methanol in DCM

出典と根拠

ORDレコード
ord-f192a86c6bd4431296b7857d74f7749c
出典データセット
uspto-grants-2011_11
特許番号
US08067408B2

反応ノート

読み込み中…