Diisopropylethylamine → HCID 178518589, compound

HRID 538034Notes

Reaction equation

HRID 538034 reaction equation
[O:1]=[C:2]1[N:11]([CH2:12][C@H:13]2[CH2:18][CH2:17][C@H:16]([C:19](O)=[O:20])[CH2:15][CH2:14]2)[C:10](=[O:22])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:56]1[CH:61]=[CH:60][CH:59]=[N:58][C:57]=1[N:62]1[CH2:67][CH2:66][NH:65][CH2:64][CH2:63]1>CN(C=O)C.CO>[N:56]1[CH:61]=[CH:60][CH:59]=[N:58][C:57]=1[N:62]1[CH2:67][CH2:66][N:65]([C:19]([C@H:16]2[CH2:15][CH2:14][C@H:13]([CH2:12][N:11]3[C:10](=[O:22])[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[NH:3][C:2]3=[O:1])[CH2:18][CH2:17]2)=[O:20])[CH2:64][CH2:63]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 887471-(2-Pyrimidinyl)piperazineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178518591HCID 178518591, compound

Product 1

HCID 178518589HCID 178518589, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of trans-4-(2,4-Dioxo-1,4-dihydro-2H-quinazolin-3-ylmethyl)-cyclohexanecarboxylic acid (100 mg, 0.33 mmol) in DMF(2 mL), diisopropylethylamine (58 μL, 0.33 mmol) and HATU (126 mg, 0.33 mmol) were added. The mixture was left 6 hours stirring at room temperature and then 1-(2-pyrimidyl)piperazine was added. After 16 hours at room temperature the solvent was removed under reduced pressure; the residue was dissolved in 2 mL of DCM and washed with 2 mL of 0.4N Na2CO3 solution. The organic layer was separated, dried over Na2SO4 and the solvent removed under reduced pressure. The titled compound (58 mg, yield 39%) was purified by precipitation from methanol.

Workup

  1. customAfter 16 hours at room temperature the solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in 2 mL of DCM
  3. washwashed with 2 mL of 0.4N Na2CO3 solution
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-f5f84d8f61b64e5abd3360479b2afb81
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

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