Diisopropylethylamine → HCID 59361937, compound

HRID 61555

Reaction equation

HRID 61555 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]([OH:11])=O)[CH2:4][CH2:3]1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:54][C:55]1[CH:56]=[C:57]([C:61]2[N:70]=[C:69]([NH:71][C:72]3[CH:73]=[C:74]4[C:78](=[CH:79][CH:80]=3)[N:77]([C:81]([O:83][C:84]([CH3:87])([CH3:86])[CH3:85])=[O:82])[N:76]=[CH:75]4)[C:68]3[C:63](=[CH:64][CH:65]=[CH:66][CH:67]=3)[N:62]=2)[CH:58]=[CH:59][CH:60]=1>C(Cl)Cl>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:8][C:9]([NH:54][C:55]2[CH:56]=[C:57]([C:61]3[N:70]=[C:69]([NH:71][C:72]4[CH:73]=[C:74]5[C:78](=[CH:79][CH:80]=4)[N:77]([C:81]([O:83][C:84]([CH3:87])([CH3:86])[CH3:85])=[O:82])[N:76]=[CH:75]5)[C:68]4[C:63](=[CH:64][CH:65]=[CH:66][CH:67]=4)[N:62]=3)[CH:58]=[CH:59][CH:60]=2)=[O:11])[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 2762732(4-Methylpiperazin-1-yl)acetic acidHCID 66825994tert-butyl 5-(2-(3-aminophenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate

Product 1

HCID 59361937HCID 59361937, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A suspension of 2-(4-methylpiperazin-1-yl)acetic acid (34 mg, 0.22 mmol), PyBOP® (11 mg, 0.22 mmol), DIEA (300 μL, 1.72 mmol) in CH2Cl2 (0.5 mL) was stirred at RT for 10-15 minutes. This solution of activated acid was added to a suspension of tert-butyl 5-(2-(3-aminophenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate (100 mg, 0.22 mmol) and CH2Cl2 (1 mL). The reaction mixture was stirred at RT for 1.5 h. Activated another 1 equivalent of the acid as described above and it was once again added to the reaction mixture. Stirred for 16 h, diluted with more CH2Cl2 and extracted with H2O (3×). Organic layer was dried under Na2SO4 and concentrated in vacuo to give the desired product tert-butyl 5-(2-(3-(2-(4-methylpiperazin-1-yl)acetamido)phenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate.

Workup

  1. stirringThe reaction mixture was stirred at RT for 1.5 h
  2. additionwas once again added to the reaction mixture
  3. stirringStirred for 16 h
  4. extractionextracted with H2O (3×)
  5. customOrganic layer was dried under Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-099752b8629947b6b90a7cd5ee89b2f0
Source dataset
uspto-grants-2016_09
Patent number
US09440961B2

Linked notes

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