Triethylamine → HCID 178452363, compound

HRID 538041Notes

Reaction equation

HRID 538041 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.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[C:54]([O:58][C:59]([N:61]1[CH2:66][CH2:65][NH:64][CH2:63][CH2:62]1)=[O:60])([CH3:57])([CH3:56])[CH3:55]>CC(N(C)C)=O>[C:54]([O:58][C:59]([N:61]1[CH2:66][CH2:65][N:64]([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])[CH2:63][CH2:62]1)=[O:60])([CH3:57])([CH3:55])[CH3:56]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 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 178452363HCID 178452363, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of trans-4-(2,4-Dioxo-1,4-dihydro-2H-quinazolin-3-ylmethyl)-cyclohexanecarboxylic acid (1.5 g, 4.96 mmol) in dimethylacetamide (10 mL), HATU (1.88 g, 4.96 mmol) and triethylamine (0.76 mL, 5.45 mmol) were added and the mixture left stirring at room temperature for 1 hour. Then tert-butyl-1-piperazinecarboxylate (0.92 g, 4.96 mmol) was added and the reaction left stirring for 18 h at room temperature. The solvent was removed under reduced pressure and the residue was washed with a 0.4M Na2CO3 solution. The titled compound was obtained as a white solid (2.3 g, quantitative yield).

Workup

  1. waitthe mixture left
  2. waitthe reaction left
  3. stirringstirring for 18 h at room temperature
  4. customThe solvent was removed under reduced pressure
  5. washthe residue was washed with a 0.4M Na2CO3 solution

Sources & evidence

ORD record
ord-118a809a1ee24ba19872b1380fd5a9a6
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

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