Triethylamine → HCID 86641345, compound

HRID 1693308Notes

Reaction equation

HRID 1693308 reaction equation
[C:1]([O:5][C:6]([N:8]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C:9]1[C:10]2[C:11]3[C:12](=[N:24][N:25]([CH2:27][C:28]4[C:33]([CH3:34])=[C:32]([O:35][CH3:36])[C:31]([CH3:37])=[CH:30][N:29]=4)[N:26]=2)[CH:13]=[C:14]([CH2:19]C(OC)=O)[C:15]=3[CH2:16][S:17][N:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P([N:59]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C>C1C=CC=CC=1>[NH2:59][CH2:19][C:14]1[C:15]2[CH2:16][S:17][N:18]=[C:9]([N:8]([C:38]([O:40][C:41]([CH3:44])([CH3:42])[CH3:43])=[O:39])[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:10]3=[N:26][N:25]([CH2:27][C:28]4[C:33]([CH3:34])=[C:32]([O:35][CH3:36])[C:31]([CH3:37])=[CH:30][N:29]=4)[N:24]=[C:12]([C:11]=23)[CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 86641343HCID 86641343, compound

Product 1

HCID 86641345HCID 86641345, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
55 °C

Procedure

A mixture composed of methyl {4-[bis(tert-butoxycarbonyl)amino]-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-2,7-dihydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-8-yl}acetate of Example 111 (121 mg), diphenylphosphoryl azide (64 μl), triethylamine (69 μl) and benzene (2 ml) was heated with stirring at a bath temperature of 55° C. for two hours. The reaction mixture was concentrated under reduced pressure. Tetrahydrofuran (8 ml) and a 1 N sodium hydroxide solution (4 ml) were added to the resulting residue, and the mixture was heated with stirring at a bath temperature of 55° C. for one hour. A 0.2 N sodium hydroxide solution was added, followed by extraction with ethyl acetate. The organic layer was dried over sodium sulfate and filtered. Then, the filtrate was concentrated under reduced pressure. The concentrated residue was purified by silica gel column chromatography (chloroform-methanol) to obtain the title compound (41 mg) as a brown oil. Although the product contained impurities, it was directly used for the next reaction without further purification.

Workup

  1. temperaturewas heated
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionTetrahydrofuran (8 ml) and a 1 N sodium hydroxide solution (4 ml) were added to the resulting residue
  4. temperaturethe mixture was heated
  5. stirringwith stirring at a bath temperature of 55° C. for one hour
  6. additionA 0.2 N sodium hydroxide solution was added
  7. extractionfollowed by extraction with ethyl acetate
  8. dry with materialThe organic layer was dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationThen, the filtrate was concentrated under reduced pressure
  11. customThe concentrated residue was purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-6b85c98f255c49cdbec5e17bd4409359
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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