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Diisopropylethylamine → 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid [2-amino-4-(4-methyl-piperazin-1-yl)-phenyl]-amide

HRID 1982945
ノート
印刷プレビュー

反応式

HRID 1982945 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]([OH:13])=O)=[N:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH3:14][N:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:22]=[C:23]([NH2:28])[C:24]([NH2:27])=[CH:25][CH:26]=2)[CH2:17][CH2:16]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[NH2:28][C:23]1[CH:22]=[C:21]([N:18]2[CH2:19][CH2:20][N:15]([CH3:14])[CH2:16][CH2:17]2)[CH:26]=[CH:25][C:24]=1[NH:27][C:11]([C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=2)[NH:8][N:9]=1)=[O:13]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 27635454-(4-Methylpiperazino)-1,2-benzenediamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178524942HCID 178524942、化合物

生成物 1

HCID 1784807545-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid [2-amino-4-(4-methyl-piperazin-1-yl)-phenyl]-amide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid Compound 1c (2.095 g, 8.66 mmol), 4-(4-methyl-piperazin-1-yl)-benzene-1,2-diamine Compound 14a (1.79 g, 8.68 mmol), HATU (3.29 g, 8.66 mmol) and DIPEA (4 mL, 28.7 mmol) in DMF (70 mL) was stirred at room temperature overnight. The solvent was removed and the residue was purified by silica gel chromatography (10% to 90% of ethyl acetate in hexanes) to yield 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid [2-amino-4-(4-methyl-piperazin-1-yl)-phenyl]-amide Compound 14b (2 g, 54% yield) as a brown powder. 1H NMR (300 MHz, CD3OD) δ 8.81 (d, 1H, J=2.1 Hz), 8.66 (d, 1H, J=2.1 Hz), 7.42 (d, 1H, J=8.7 Hz), 7.11 (dd, 1H, J=2.7, 8.7 Hz), 7.03 (d, 1H, J=2.7 Hz), 3.92 (b, 2H), 3.65 (b, 2H), 3.31 (b, 2H), 3.16 (b, 2H), 2.81 (s, 3H); MS (ESI) m/z: 431 (M+H+).

後処理

  1. customThe solvent was removed
  2. customthe residue was purified by silica gel chromatography (10% to 90% of ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-2ee26248124748e8834803e5fe590edb
出典データセット
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07541367B2

反応ノート

読み込み中…

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