Ammonia → HCID 68185409, compound

HRID 2366900Notes

Reaction equation

HRID 2366900 reaction equation
[CH3:1][CH:2]([O:4][C:5](=[O:22])[NH:6][C@H:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14](Br)[CH:15]=2)[N:10]([C:18](=[O:20])[CH3:19])[C@@H:9]([CH3:21])[CH2:8]1)[CH3:3].[NH3:23]>CN(C)C=O.[Cu-]=O>[CH3:1][CH:2]([O:4][C:5](=[O:22])[NH:6][C@H:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([NH2:23])[CH:15]=2)[N:10]([C:18](=[O:20])[CH3:19])[C@@H:9]([CH3:21])[CH2:8]1)[CH3:3]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 529350201-Methylethyl((cis)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl)carbamate

Product 1

HCID 68185409HCID 68185409, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1-methylethyl[(2S,4R)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see example 4) (2.71 g, 7.34 mmol) and copper(I) oxide (0.247 g, 1.726 mmol) in N,N-dimethylformamide (DMF) (5 mL) was treated with NH3 (35% w/w in water) (5 mL, 258 mmol) and the resulting mixture was stirred at 110° C. for 5 h under microwave irradiation then cooled to room temperature and concentrated in vacuo. The residue was partitioned between water and AcOEt and the layers were separated. The aqueous phase was extracted with AcOEt (2×50 mL) and the combined organic phases were dried over MgSO4 then concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (gradient: 10 to 100% AcOEt in Hexanes) gave 1-methylethyl[(2S,4R)-1-acetyl-6-amino-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (1.91 g, 6.25 mmol, 85%) as an orange foamy solid.

Workup

  1. temperaturethen cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between water and AcOEt
  4. customthe layers were separated
  5. extractionThe aqueous phase was extracted with AcOEt (2×50 mL)
  6. dry with materialthe combined organic phases were dried over MgSO4
  7. concentrationthen concentrated in vacuo
  8. customPurification of the residue by flash chromatography on silica gel (gradient: 10 to 100% AcOEt in Hexanes)

Sources & evidence

ORD record
ord-68fe023498624798a813dc3c51fcbcf5
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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