Diisopropylethylamine → 1-(6-(5-fluoroindoline-1-carbonyl)pyrimidin-4-yl)spiro[piperidine-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one

HRID 1640272Notes

Reaction equation

HRID 1640272 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([F:19])=[CH:16][CH:17]=3)[CH2:12][CH2:11]2)=[O:9])[CH:3]=1.Cl.[NH:21]1[C:26]2[N:27]=[CH:28][CH:29]=[CH:30][C:25]=2[C:24]2([CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[O:23][C:22]1=[O:36].CCN(C(C)C)C(C)C>CN(C=O)C>[F:19][C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[N:10]([C:8]([C:4]1[N:5]=[CH:6][N:7]=[C:2]([N:33]3[CH2:32][CH2:31][C:24]4([O:23][C:22](=[O:36])[NH:21][C:26]5[N:27]=[CH:28][CH:29]=[CH:30][C:25]4=5)[CH2:35][CH2:34]3)[CH:3]=1)=[O:9])[CH2:11][CH2:12]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 58117506(6-Chloro-pyrimidin-4-yl)-(5-fluoro-2,3-dihydro-indol-1-yl)-methanoneHCID 66687106Spiro[piperidine-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one hydrochloride

Product 1

HCID 581174781-(6-(5-fluoroindoline-1-carbonyl)pyrimidin-4-yl)spiro[piperidine-4,4'-pyrido[2,3-d][1,3]oxazin]-2'(1'H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.10 g (0.36 mmol) (6-chloro-pyrimidin-4-yl)-(5-fluoro-2,3-dihydro-indol-1-yl)-methanone were added to 92 mg (0.36 mmol) spiro[piperidine-4,4′-pyrido[2,3-d][1,3]oxazin]-2′(1′H)-one-hydrochloride and 146 μL (0.84 mmol) DIPEA in 1.8 mL DMF. The reaction mixture was stirred overnight at RT. Then the reaction mixture was purified by preparative HPLC-MS. The product fractions were combined and lyophilised.

Workup

  1. customThen the reaction mixture was purified by preparative HPLC-MS

Sources & evidence

ORD record
ord-45421bb3cf494b5d95ce255a3820d649
Source dataset
uspto-grants-2012_02
Patent number
US08110575B2

Reaction notes

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