Triethylamine → HCID 69652414, compound

HRID 2212208Notes

Reaction equation

HRID 2212208 reaction equation
[CH:1]1[CH:6]=[N:5][C:4]2N(O)N=N[C:3]=2[CH:2]=1.C[CH2:12][N:13]=C=NCCCN(C)C.CCN(CC)CC.[C:29]([O:33][C:34]([N:36]1[CH2:41][CH:40]([N:42]2[C:51]3[CH:50]=[CH:49][CH:48]=[C:47]([Cl:52])[C:46]=3[C:45]3=[N:53][O:54][C:55]([CH3:56])=[C:44]3[C:43]2=[O:57])[CH2:39][CH:38]([C:58](O)=[O:59])[CH2:37]1)=[O:35])([CH3:32])([CH3:31])[CH3:30]>CN(C1C=CN=CC=1)C.CN(C=O)C>[C:29]([O:33][C:34]([N:36]1[CH2:37][CH:38]([C:58](=[O:59])[NH:13][CH2:12][C:3]2[CH:4]=[N:5][CH:6]=[CH:1][CH:2]=2)[CH2:39][CH:40]([N:42]2[C:51]3[CH:50]=[CH:49][CH:48]=[C:47]([Cl:52])[C:46]=3[C:45]3=[N:53][O:54][C:55]([CH3:56])=[C:44]3[C:43]2=[O:57])[CH2:41]1)=[O:35])([CH3:31])([CH3:32])[CH3:30]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 69652404HCID 69652404, compound

Product 1

HCID 69652414HCID 69652414, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

Add HOAt (30 mg, 0.22 mmol), EDCI (41 mg, 0.22 mmol), Et3N (0.075 mL, 0.54 mmol), and DMAP (5 mg, cat.) to a solution of 5-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester (83 mg, 0.18 mmol) in DMF (5 mL). Stir overnight at room temperature and concentrate to dryness. Dissolve in 20% iPrOH/CHCl3. Wash 2× sat. aq NaHCO3, wash 2× with brine, dry over Na2SO4, filter, and concentrate to dryness. Purify by radial chromatography using a MeOH/CHCl3 gradient as eluant and concentrate to dryness. Slurry the residue in ether/hexanes and concentrate to dryness to afford the title compound (44 mg, 50%) as a white foam as a mixture of cis isomers. MS(IS) 552.2 (M+); HPLC (100% EtOH 0.2% DMEA on a Chiralpak AD (0.46×25 cm) 1.0 mL/min flow; 20 μL Inj. Vol.; 225 nM) Rt=6.291 min (67.8%), 13.156 min (24.4%).

Workup

  1. concentrationconcentrate to dryness
  2. dissolutionDissolve in 20% iPrOH/CHCl3
  3. washWash 2× sat. aq NaHCO3
  4. washwash 2× with brine
  5. dry with materialdry over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate to dryness
  8. customPurify by radial chromatography
  9. concentrationconcentrate to dryness
  10. concentrationconcentrate to dryness

Sources & evidence

ORD record
ord-75bc0cb9f8a541e49e9f0e4d7dd1ea16
Source dataset
uspto-grants-2006_09
Patent number
US07101891B2

Reaction notes

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