Triethylamine → HCID 470751, compound

HRID 724957Notes

Reaction equation

HRID 724957 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:31])[C:7](=[O:30])[C:8]3[CH:18]=[C:17]([CH2:19][CH2:20][C:21]4[CH:26]=[CH:25][N:24]=[C:23](C(O)=O)[CH:22]=4)[CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1.CC[N:34](CC)CC.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>C(O)(C)(C)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:31])[C:7](=[O:30])[C:8]3[CH:18]=[C:17]([CH2:19][CH2:20][C:21]4[CH:26]=[CH:25][N:24]=[C:23]([NH2:34])[CH:22]=4)[CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 470750HCID 470750, compound

Product 1

HCID 470751HCID 470751, compoundYield 16.3%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of 2-chloro-5,11-dihydro-11-ethyl-5-methyl-8-[2-(2-carboxypyrid-4-yl)ethyl]-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (92 mg, 0.21 mmol) and Et3N (0.03 mL, 0.22 mmol) in t-butanol (20 mL) was added diphenylphosphoryl azide (0.046 g, 0.21 mmol). The reaction mixture was heated at reflux under argon for 16 hours. Solvents were removed by rotary evaporation, and the residue was dissolved in ethyl acetate, washed with saturated aq. sodium bicarbonate, dried (magnesium sulfate), and concentrated. The residue was treated with 2N hydrochloric acid in ethanol at 25°-50° C. for 30 hours. The reaction mixture was concentrated, basified with 6N sodium hydroxide, and extracted with ethyl acetate. Purification by flash chromatography (elution with methanol-dichloromethane) and recrystallization (diethyl ether-petroleum ether) afforded 14 mg (16%) of the title compound, m.p. 95° C. (dec).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux under argon for 16 hours
  3. customSolvents were removed by rotary evaporation
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washwashed with saturated aq. sodium bicarbonate
  6. dry with materialdried (magnesium sulfate)
  7. concentrationconcentrated
  8. additionThe residue was treated with 2N hydrochloric acid in ethanol at 25°-50° C. for 30 hours
  9. concentrationThe reaction mixture was concentrated
  10. extractionextracted with ethyl acetate
  11. customPurification
  12. washby flash chromatography (elution with methanol-dichloromethane) and recrystallization (diethyl ether-petroleum ether)

Sources & evidence

ORD record
ord-9361fd2fcb634e8c8da08944e6df602c
Source dataset
uspto-grants-1998_01
Patent number
US05705499

Reaction notes

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