Diisopropylethylamine → HCID 178473918, compound

HRID 538062Notes

Reaction equation

HRID 538062 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][C:4](=[O:12])[N:3]1[CH2:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([C:20]([OH:22])=O)[CH2:16][CH2:15]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[C:56]([N:59]1[CH2:64][CH2:63][NH:62][CH2:61][CH2:60]1)(=[O:58])[CH3:57]>CN(C)C(=O)C>[C:56]([N:59]1[CH2:64][CH2:63][N:62]([C:20]([C@H:17]2[CH2:18][CH2:19][C@H:14]([CH2:13][N:3]3[C:4](=[O:12])[CH2:5][C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[C:2]3=[O:1])[CH2:15][CH2:16]2)=[O:22])[CH2:61][CH2:60]1)(=[O:58])[CH3:57]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 837951-AcetylpiperazineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178515328HCID 178515328, compound

Product 1

HCID 178473918HCID 178473918, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

trans-4-(1,3-Dioxo-3,4-dihydro-1H-isoquinolin-2-ylmethyl)-cyclo hexanecarboxylic acid (100 mg, 0.33 mmol) was dissolved in N,N-dimethyl acetamide (3 mL), HATU (125 mg, 0.33 mmol) and diisopropyl ethylamine (0.06 mL, 0.33 mmol) were added and the mixture was left stirring for 1 h. Then 1-acetylpiperazine (128 mg, 0.3 mmol) was added and the reaction stirred for 18 hours. The solvent was removed under reduced pressure and the residue was dissolved in 2 mL of DCM and washed with 2 mL of 0.4M Na2CO3 solution. The organic phase was collected and the solvent removed under reduced pressure. The crude was purified by SiO2 column, eluting with DCM-MeOH (97:3) and the fractions containing the desired product collected and further purified by prep HPLC. 42 mg of the title product were obtained (31% yield).

Workup

  1. waitthe mixture was left
  2. stirringthe reaction stirred for 18 hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in 2 mL of DCM
  5. washwashed with 2 mL of 0.4M Na2CO3 solution
  6. customThe organic phase was collected
  7. customthe solvent removed under reduced pressure
  8. customThe crude was purified by SiO2 column
  9. washeluting with DCM-MeOH (97:3)
  10. additionthe fractions containing the desired product
  11. customcollected
  12. customfurther purified by prep HPLC

Sources & evidence

ORD record
ord-de3b87f399cb409db51bfe1642897dd1
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

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