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1-Methylpiperazine → 2-(4-(1H-indazol-5-ylamino)-2-[(3-phenyl)phenyl)-7-methoxyquinazolin-6-yloxy)-1-(4-methylpiperazin-1-yl)ethanone

HRID 1808481
Notes
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Reaction equation

HRID 1808481 reaction equation
N1C2C(=CC([NH:10][C:11]3[C:20]4[C:15](=[CH:16][C:17]([O:26][CH3:27])=[C:18]([O:21][CH2:22][C:23](O)=[O:24])[CH:19]=4)[N:14]=[C:13]([C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)[CH:29]=4)[N:12]=3)=CC=2)C=N1.C1CN([P+](ON2[N:65]=[N:64][C:59]3[CH:60]=[CH:61][CH:62]=[CH:63][C:58]2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[CH3:73]CN(C(C)C)C(C)C.[CH3:82][N:83]1[CH2:88][CH2:87][NH:86][CH2:85][CH2:84]1>CN(C=O)C.C(Cl)Cl>[NH:64]1[C:59]2[C:58](=[CH:63][C:62]([NH:10][C:11]3[C:20]4[C:15](=[CH:16][C:17]([O:26][CH3:27])=[C:18]([O:21][CH2:22][C:23]([N:86]5[CH2:87][CH2:88][N:83]([CH3:82])[CH2:84][CH2:85]5)=[O:24])[CH:19]=4)[N:14]=[C:13]([C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)[CH:29]=4)[N:12]=3)=[CH:61][CH:60]=2)[CH:73]=[N:65]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 59361846HCID 59361846, compound

Product 1

HCID 497796222-(4-(1H-indazol-5-ylamino)-2-[(3-phenyl)phenyl)-7-methoxyquinazolin-6-yloxy)-1-(4-methylpiperazin-1-yl)ethanoneYield 5%

Reagents, catalysts & solvents

2
HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-(4-(1H-indazol-5-ylamino)-2-[(3-phenyl)phenyl)-7-methoxyquinazolin-6-yloxy)acetic acid (0.25 g, 0.48 mmole) in DMF (1 mL)/CH2Cl2 (7 mL) was added PyBOP® (0.25 g, 0.48 mmole), and DIEA (0.186 g, 0.251 mL, 1.44 mmole). The mixture was then stirred for 15 minutes and 1-methylpiperazine (0.048 g, 0.053 mL, 0.48 mmole) was added and the reaction was stirred at RT for 3 h. The volatiles were then removed in vacuo. Upon adding CH2Cl2, the crude product precipitated and was subsequently filtered. The cake was washed with ether, hexane, CH3OH, CH2Cl2 and finally hexane. The crude product was purified by reverse phase HPLC (25 to 55% CH3CN/H2O, 90 minute run time) to yield 2-(4-(1H-indazol-5-ylamino)-2-[(3-phenyl)phenyl)-7-methoxyquinazolin-6-yloxy)-1-(4-methylpiperazin-1-yl)ethanone (0.015 g, 5%). MS 600 (M+1). HPLC retention time 5.22 mins.

Workup

  1. stirringthe reaction was stirred at RT for 3 h
  2. customThe volatiles were then removed in vacuo
  3. additionUpon adding CH2Cl2
  4. customthe crude product precipitated
  5. filtrationwas subsequently filtered
  6. washThe cake was washed with ether, hexane, CH3OH, CH2Cl2 and finally hexane
  7. customThe crude product was purified by reverse phase HPLC (25 to 55% CH3CN/H2O, 90 minute run time)

Sources & evidence

ORD record
ord-90b016a1d7194a70adc3b87cdbaf9713
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08357693B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes