Diisopropylethylamine → HCID 118699716, compound

HRID 1773311Notes

Reaction equation

HRID 1773311 reaction equation
Cl.[CH3:2][O:3][C:4]1[C:5]([O:27][CH3:28])=[CH:6][C:7]2[C:16]3[CH2:15][CH2:14][N:13]([C:17]4[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=4)[C:20](O)=[O:21])[CH2:12][C:11]=3[CH:10]=[N:9][C:8]=2[CH:26]=1.C(N(CC)C(C)C)(C)C.CCCP(=O)=O.[CH:44]([C:47]1[CH:48]=[C:49]([CH:51]=[CH:52][CH:53]=1)[NH2:50])([CH3:46])[CH3:45]>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH3:2][O:3][C:4]1[C:5]([O:27][CH3:28])=[CH:6][C:7]2[C:16]3[CH2:15][CH2:14][N:13]([C:17]4[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=4)[C:20]([NH:50][C:49]4[CH:51]=[CH:52][CH:53]=[C:47]([CH:44]([CH3:46])[CH3:45])[CH:48]=4)=[O:21])[CH2:12][C:11]=3[CH:10]=[N:9][C:8]=2[CH:26]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 4586793-Isopropylaniline2×HCID 16167369Propylphosphoric anhydride2×HCID 118699725HCID 118699725, compound

Product 1

HCID 118699716HCID 118699716, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-(8,9-dimethoxy-1,4-dihydrobenzo[c]-2,7-naphthyridin-3(2H)-yl)benzoic acid hydrochloride (0.25 mmol, 100 mg) and N, N-diisopropylethylamine (0.75 mmol, 0.131 mL) in 2.0 mL DMF at rt was added propylphosphonic anhydride solution (50 wt % in EtOAc, 0.325 mmol, 0.193 mL). After 5 min at rt, 3-isopropylaniline (0.375 mmol, 0.053 mL) and catalytic DMAP was added and the reactions continued for 2 hours. Then an additional 0.050 mL propylphosphonic anhydride solution and 0.025 mL 3-isopropylaniline was added and the reaction continued for 19 hours. The reaction was quenched into dilute aqueous Na2CO3 solution, extracted into EtOAc, the EtOAc layer washed with H2O, brine, dried with anhydrous Na2SO4 and rotary evaporated. The resulting oil was chromatographed eluting with CHCl3/EtOAc and then recrystallized from EtOAc/hexane to give the title compound as a white solid (20 mg, 17%).

Workup

  1. waitthe reactions continued for 2 hours
  2. waitthe reaction continued for 19 hours
  3. customThe reaction was quenched into dilute aqueous Na2CO3 solution
  4. extractionextracted into EtOAc
  5. washthe EtOAc layer washed with H2O, brine
  6. dry with materialdried with anhydrous Na2SO4 and rotary evaporated
  7. customThe resulting oil was chromatographed
  8. washeluting with CHCl3/EtOAc
  9. customrecrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-dc42d6ea318746c39aab38011e8522ca
Source dataset
uspto-grants-2016_02
Patent number
US09255096B1

Reaction notes

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