Diisopropylethylamine → (1S,2S,3R,4R)-3-(2-Amino-5-chloro-3-nitro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide

HRID 591915Notes

Reaction equation

HRID 591915 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[C:4]([NH2:9])[C:3]=1[N+:10]([O-:12])=[O:11].FC(F)(F)C(O)=O.[NH2:20][C@@H:21]1[C@@H:26]2[CH2:27][C@@H:23]([CH:24]=[CH:25]2)[C@@H:22]1[C:28]([NH2:30])=[O:29].C(N(CC)C(C)C)(C)C>C(O)(C)C>[NH2:9][C:4]1[C:3]([N+:10]([O-:12])=[O:11])=[C:2]([NH:20][C@@H:21]2[C@@H:26]3[CH2:27][C@@H:23]([CH:24]=[CH:25]3)[C@@H:22]2[C:28]([NH2:30])=[O:29])[C:7]([Cl:8])=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 468676602-Amino-4,5-dichloro-3-nitropyridineHCID 67264207(1S,2S,3R,4R)-3-Amino-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide trifluoroacetic acid salt

Product 1

HCID 117701942(1S,2S,3R,4R)-3-(2-Amino-5-chloro-3-nitro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amideYield 95%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

4,5-Dichloro-3-nitro-pyridin-2-ylamine (1.01 g, 4.86 mmol) and (1S,2S,3R,4R)-3-Amino-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide trifluoroacetic acid salt (1.5 g, 5.5 mmol) were combined with N,N-diisopropylethylamine (3.3 g, 26 mmol) in isopropanol (15 mL) and heated at 60° C. overnight. The reaction was permitted to cool to room temperature and the orange solid which had formed was isolated by filtration. The solid was washed with 3 mL cold isopropanol and was dried in an air stream to afford 1.493 g (95%) of the desired product.

Workup

  1. temperatureto cool to room temperature
  2. customthe orange solid which had formed
  3. customwas isolated by filtration
  4. washThe solid was washed with 3 mL cold isopropanol
  5. customwas dried in an air stream

Sources & evidence

ORD record
ord-907401a30dbb4a4db2b6256fb1234200
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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