Triethylamine hydrochloride → HCID 86760800, compound

HRID 2378113Notes

Reaction equation

HRID 2378113 reaction equation
[CH:1]([O:4][C:5]([N:7]1[C:16]2[C:11](=[N:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C@H:10]([N:19]([CH2:22][C:23]2[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[C:25]([C:33]([F:36])([F:35])[F:34])[CH:24]=2)[C:20]#[N:21])[CH2:9][C@@H:8]1[CH2:37][CH3:38])=[O:6])([CH3:3])[CH3:2].[N-:39]=[N+:40]=[N-:41].[Na+].Cl.C(N(CC)CC)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH:1]([O:4][C:5]([N:7]1[C:16]2[C:11](=[N:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C@H:10]([N:19]([CH2:22][C:23]2[CH:24]=[C:25]([C:33]([F:36])([F:35])[F:34])[CH:26]=[C:27]([C:29]([F:30])([F:31])[F:32])[CH:28]=2)[C:20]2[N:39]=[N:40][NH:41][N:21]=2)[CH2:9][C@@H:8]1[CH2:37][CH3:38])=[O:6])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 11130Triethylamine hydrochloride2×HCID 33557Sodium Azide2×HCID 86760801HCID 86760801, compound

Product 1

HCID 86760800HCID 86760800, compoundYield 56.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

Heat at 120° C. a mixture of (+/−)-cis-4-[(3,5-bis-trifluoromethyl-benzyl)-cyano-amino]-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid isopropyl ester (100 mg, 0.184 mmol), sodium azide (17 mg, 0.258 mmol) and triethyl amine hydrochloride (35 mg, 0.258 mmol) in dry toluene under an atmosphere of nitrogen for 8 h. Then add more sodium azide (6 mg) and triethyl amine hydrochloride (13 mg) and heat the mixture for 4 h. Cool to room temperature, dilute with ethyl acetate, and wash with 1 N HCl. Dry the organic layer over anhydrous sodium sulfate, filter, and remove the solvent under reduced pressure. Purify the residue by flash chromatography, eluting with hexanes/ethyl acetate, to afford the title compound (61 mg, 50%). MS (ES+): 588 (M+H).

Workup

  1. temperatureheat the mixture for 4 h
  2. temperatureCool to room temperature
  3. washwash with 1 N HCl
  4. dry with materialDry the organic layer over anhydrous sodium sulfate
  5. filtrationfilter
  6. customremove the solvent under reduced pressure
  7. customPurify the residue by flash chromatography
  8. washeluting with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-e7387915dbef4b4c95159735b8c3aa9d
Source dataset
uspto-grants-2008_12
Patent number
US07470705B2

Reaction notes

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