Potassium Carbonate → 4-tert-Butyloxycarbonylamino-1-(6-methoxy-[1,5]naphthyridin-4-yl)aminocarbonylpiperidine

HRID 1271680Notes

Reaction equation

HRID 1271680 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[N:10]=2)[N:5]=[CH:4][CH:3]=1.C1N=CN([C:19]([N:21]2[CH:25]=N[CH:23]=[CH:22]2)=[O:20])C=1.Cl.[C:27]([O:31][C:32]([NH:34][CH:35]1CCNC[CH2:36]1)=[O:33])([CH3:30])([CH3:29])[CH3:28].C(=O)([O-])[O-].[K+].[K+]>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[C:27]([O:31][C:32]([NH:34][CH:35]1[CH2:23][CH2:22][N:21]([C:19]([NH:1][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[N:10]=3)[N:5]=[CH:4][CH:3]=2)=[O:20])[CH2:25][CH2:36]1)=[O:33])([CH3:30])([CH3:29])[CH3:28]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 682631,1'-CarbonyldiimidazoleHCID 27560284-(tert-Butoxycarbonylamino)piperidine hydrochlorideHCID 114352366-Methoxy-1,5-naphthyridin-4-amine

Product 1

HCID 222817154-tert-Butyloxycarbonylamino-1-(6-methoxy-[1,5]naphthyridin-4-yl)aminocarbonylpiperidine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 4-amino-6-methoxy-[1,5]naphthyridine (7a) (2.1 g, 13.5 mmol) and 4-(dimethylamino)pyridine (1.62 g) in anhydrous chloroform (45 ml) was added N,N-carbonyldiimidazole (3.28 g, 20.1 mmol). The mixture was stirred for 4 hours at room temperature, then evaporated and the residue was dissolved in anhydrous N,N-dimethylformamide (45 ml). 4-tert-Butoxycarbonylaminopiperidine hydrochloride (3.34 g, 13.5 mmol) and potassium carbonate (1.89 g) were added, and the mixture was heated at 70° C. overnight. The mixture was evaporated and the residue was mixed with water (120 ml). The solid was filtered off and dried (3.89 g).

Workup

  1. customevaporated
  2. dissolutionthe residue was dissolved in anhydrous N,N-dimethylformamide (45 ml)
  3. temperaturethe mixture was heated at 70° C. overnight
  4. customThe mixture was evaporated
  5. additionthe residue was mixed with water (120 ml)
  6. filtrationThe solid was filtered off
  7. customdried (3.89 g)

Sources & evidence

ORD record
ord-e433ae13d5eb4f17aa4ccbced7c2465b
Source dataset
uspto-grants-2007_04
Patent number
US07205408B2

Reaction notes

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