Sulfuric Acid → HCID 178481611, compound

HRID 538044Notes

Reaction equation

HRID 538044 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[N:4]([CH2:13][C@H:14]2[CH2:19][CH2:18][C@H:17]([C:20]([OH:22])=O)[CH2:16][CH2:15]2)[C:3]1=[O:23].CCN(C(C)C)C(C)C.CN(C(ON1N=[N:48][C:43]2C=[CH:45][CH:46]=[N:47][C:42]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N1CCNCC1)(OC(C)(C)C)=O.OS(O)(=O)=O>CN(C=O)C.C(Cl)Cl>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[N:4]([CH2:13][C@H:14]2[CH2:19][CH2:18][C@H:17]([C:20]([N:47]3[CH2:42][CH2:43][NH:48][CH2:45][CH2:46]3)=[O:22])[CH2:16][CH2:15]2)[C:3]1=[O:23]

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 81531DiisopropylethylamineHCID 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 178481614HCID 178481614, compound

Product 1

HCID 178481611HCID 178481611, compoundYield 463.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

trans-4-(1-Methyl-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-ylmethyl)-cyclohexanecarboxylic acid (1.0 g, 3.2 mmol), DIPEA (560 μL, 3.2 mmol), HATU (1.2 g, 0.32 mmol) were dissolved in 20 ml of DMF. The mixture was stirred at room temperature for 2 hours and then 14 ml of the solution were transferred in a different flask. To this solution Boc-piperazine (411 mg, 2.2 mmol) was added and the mixture was stirred at room temperature for 18 hours. The solvent was removed under reduced pressure and the residue dissolved in DCM and washed with 0.4 M solution of Na2CO3. The organic phase was separated and the solvent removed under reduced pressure to give 900 mg of crude boc protected intermediate. The compound was dissolved in 10 ml of DCM, 255 μL of H2SO4 were added and the mixture was left stirring at room temperature for 18 hours. The solution was washed with a solution of NaOH (10% W/W), the organic phase was separated and concentrated under reduced pressure to give 570 mg (yield 80%) of the titled compound.

Workup

  1. stirringthe mixture was stirred at room temperature for 18 hours
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue dissolved in DCM
  4. washwashed with 0.4 M solution of Na2CO3
  5. customThe organic phase was separated
  6. customthe solvent removed under reduced pressure
  7. customto give 900 mg of crude boc protected intermediate
  8. waitthe mixture was left
  9. stirringstirring at room temperature for 18 hours
  10. washThe solution was washed with a solution of NaOH (10% W/W)
  11. customthe organic phase was separated
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-35add13c84be4cec8a225e3b474f7a7b
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

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