Potassium Carbonate → HCID 67345240, compound

HRID 1630352Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]3[CH:13]=[N:14][C:15]4[C:20]([CH:21]=3)=[CH:19][CH:18]=[CH:17][CH:16]=4)[N:10]=2)[N:5]=[CH:4][C:3]=1[C:22]([O:24][CH2:25]C)=[O:23].[NH2:27][CH:28]1[CH2:33][CH2:32][N:31]([C:34]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:35])[CH2:30][CH2:29]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C>[CH2:37]([O:36][C:34]([N:31]1[CH2:30][CH2:29][CH:28]([NH:27][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([C:12]4[CH:13]=[N:14][C:15]5[C:20]([CH:21]=4)=[CH:19][CH:18]=[CH:17][CH:16]=5)[N:10]=3)[N:5]=[CH:4][C:3]=2[C:22]([O:24][CH3:25])=[O:23])[CH2:33][CH2:32]1)=[O:35])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of ethyl 4-chloro-6-quinolin-3-yl-1,5-naphthyridine-3-carboxylate (compound 41) (6.0 g, 17 mmol), 4-amino-1-N-Cbz-piperidine (compound 45) (4.1 g, 17 mmol), and potassium carbonate (4.6 g, 33 mmol) in N,N-dimethylacetamide (100 mL) was heated to 90° C. After 2 hours, the reaction was cooled to room temperature and filtered. The filtrate was concentrated and the residue was triturated with methanol to afford methyl 4-({1-[(benzyloxy)carbonyl]piperidin-4-yl}amino)-6-quinolin-3-yl-1,5-naphthyridine-3-carboxylate (compound 46) as a cream solid (8.2 g, 90%).

Workup

temperaturethe reaction was cooled to room temperature
filtrationfiltered
concentrationThe filtrate was concentrated
customthe residue was triturated with methanol

Sources & evidence

ORD record: ord-daae9beb29774cbdb6d3e13bd0f884ae
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791131B2

Reaction notes

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