Triethylamine → HCID 66905396, compound

HRID 1967469Notes

Reaction equation

HRID 1967469 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](Cl)=[N:6][CH:7]=1.Cl.[NH2:13][CH2:14][CH2:15][C@H:16]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].C(N(CC)CC)C>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([NH:13][CH2:14][CH2:15][CH:16]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:17]([O:19][C:20]([CH3:22])([CH3:23])[CH3:21])=[O:18])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70194125-Bromo-2-chloro-3-nitropyridineHCID 56777080HCID 56777080, compound

Product 1

HCID 66905396HCID 66905396, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A procedure similar to the method described in step C.1 is carried out, starting from 2 g (8.42 mmol) of 5-bromo-2-chloro-3-nitropyridine, 3.14 g (10.11 mmol) of tert-butyl (S)-4-amino-2-tert-butoxycarbonylaminobutanoate hydrochloride and 2.31 g (16.85 mmol) of triethylamine in 30 ml of dioxane. This time the mixture is heated for 12 hours. This gives 3.71 g of the expected product, which is used as it is in the remainder of the synthesis.

Workup

  1. temperatureThis time the mixture is heated for 12 hours

Sources & evidence

ORD record
ord-61d42f6800314943acbd5dcd8aa2e2c0
Source dataset
uspto-grants-2013_04
Patent number
US08420817B2

Reaction notes

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