Triethylamine → HCID 86642103, compound

HRID 1943203Notes

Reaction equation

HRID 1943203 reaction equation
[NH2:1][C:2]1([CH3:23])[CH2:7][CH2:6][N:5]([CH2:8][C@H:9]2[N:19]3[C:20]4[N:11]([C:12](=[O:22])[CH2:13][CH2:14][C:15]=4[CH:16]=[CH:17][C:18]3=[O:21])[CH2:10]2)[CH2:4][CH2:3]1.C(N(CC)CC)C.[C:31](=O)(O)[O-:32].[Na+]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[N:1]([C:2]1([CH3:23])[CH2:3][CH2:4][N:5]([CH2:8][C@H:9]2[N:19]3[C:20]4[N:11]([C:12](=[O:22])[CH2:13][CH2:14][C:15]=4[CH:16]=[CH:17][C:18]3=[O:21])[CH2:10]2)[CH2:6][CH2:7]1)=[C:31]=[O:32]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 68596222HCID 68596222, compound

Product 1

HCID 86642103HCID 86642103, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of (1R)-1-[(4-amino-4-methyl-1-piperidinyl)methyl]-1,2,5,6-tetrahydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dione (1.294 g, 4.09 mmol) in DCM (30 ml) under argon at rt was treated with triethylamine (0.684 ml, 4.91 mmol), then di-tent-butyl dicarbonate (1.045 ml, 4.50 mmol) and finally 4-dimethylaminopyridine (0.050 g, 0.409 mmol) and stirred at rt for 1 h. The reaction mixture was treated with aq sodium bicarbonate (100 ml) and extracted with DCM (3×200 ml). The combined organic fractions were dried (MgSO4), filtered and evaporated to give the crude product as a yellow solid which was then chromatographed (0-10% methanol/DCM, Rf=0.5 in 10% methanol/DCM) to give the product as a white solid (561 mg, 40%).

Workup

  1. extractionextracted with DCM (3×200 ml)
  2. dry with materialThe combined organic fractions were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customto give the crude product as a yellow solid which
  6. customwas then chromatographed (0-10% methanol/DCM, Rf=0.5 in 10% methanol/DCM)

Sources & evidence

ORD record
ord-f540d029e2e4469295c5b56806161bff
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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