Diisopropylethylamine → HCID 56949456, compound

HRID 61550Notes

Reaction equation

HRID 61550 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]([OH:10])=O)[CH2:3][CH2:2]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.[NH2:53][C:54]1[CH:55]=[C:56]([C:60]2[N:69]=[C:68]([NH:70][C:71]3[CH:72]=[C:73]4[C:77](=[CH:78][CH:79]=3)[N:76]([C:80]([O:82][C:83]([CH3:86])([CH3:85])[CH3:84])=[O:81])[N:75]=[CH:74]4)[C:67]3[C:62](=[CH:63][CH:64]=[CH:65][CH:66]=3)[N:61]=2)[CH:57]=[CH:58][CH:59]=1>C(Cl)Cl>[O:1]1[CH2:2][CH2:3][N:4]([CH2:7][C:8]([NH:53][C:54]2[CH:55]=[C:56]([C:60]3[N:69]=[C:68]([NH:70][C:71]4[CH:72]=[C:73]5[C:77](=[CH:78][CH:79]=4)[N:76]([C:80]([O:82][C:83]([CH3:86])([CH3:85])[CH3:84])=[O:81])[N:75]=[CH:74]5)[C:67]4[C:62](=[CH:63][CH:64]=[CH:65][CH:66]=4)[N:61]=3)[CH:57]=[CH:58][CH:59]=2)=[O:10])[CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 4389684-Morpholineacetic acidHCID 2724699PyBOPHCID 66825994tert-butyl 5-(2-(3-aminophenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate

Product 1

HCID 56949456HCID 56949456, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A suspension of 2-morpholinoacetic acid (16 mg, 0.11 mmol), PyBOP (57 mg, 0.11 mmol), DIEA (96 μL, 0.55 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 0.5 equivalent of the acid as described above and it was once again added to the reaction mixture and stirred for 1.5 h. Added two more 0.5 equivalents of activated acid while stirring 1.5 hr between each addition. Diluted with more CH2Cl2 and extracted with H2O (3×). Organic layer was dried under Na2SO4 and concentrated in vacuo to give the desired oil product tert-butyl 5-(2-(3-(2-morpholinoacetamido)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 1.5 h
  4. stirringwhile stirring 1.5 hr between each addition
  5. extractionextracted with H2O (3×)
  6. customOrganic layer was dried under Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b9c2bdc062064ce59946199df20ac5dc
Source dataset
uspto-grants-2016_09
Patent number
US09440961B2

Reaction notes

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