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

HRID 1062702Notes

Reaction equation

HRID 1062702 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 (Example 400a) (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 h at room temperature, then evaporated and the residue was dissolved in anhydrous DMF (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 DMF (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-e1e7f16a5d67470bb586740b4d987bf9
Source dataset
uspto-grants-2005_11
Patent number
US06962917B2

Reaction notes

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