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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
Notes
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Reaction equation

HRID 1982945 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 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, compound

Product 1

HCID 178480754
5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid [2-amino-4-(4-methyl-piperazin-1-yl)-phenyl]-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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+).

Workup

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

Sources & evidence

ORD record
ord-2ee26248124748e8834803e5fe590edb
Source dataset
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07541367B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes