Potassium Carbonate → 1-(4-(4,5-difluoroindoline-1-carbonyl)pyridin-2-yl)spiro[piperidine-4,4'-pyrido[2,3-d][1,3]-oxazin]-2'(1'H)-one

HRID 1640277Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([C:8]([N:10]2[C:18]3[C:13](=[C:14]([F:20])[C:15]([F:19])=[CH:16][CH:17]=3)[CH2:12][CH2:11]2)=[O:9])[CH:5]=[CH:4][N:3]=1.Cl.[NH:22]1[C:27]2[N:28]=[CH:29][CH:30]=[CH:31][C:26]=2[C:25]2([CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[O:24][C:23]1=[O:37].C(=O)([O-])[O-].[K+].[K+].O.C(#N)C>CN1C(=O)CCC1>[F:20][C:14]1[C:15]([F:19])=[CH:16][CH:17]=[C:18]2[C:13]=1[CH2:12][CH2:11][N:10]2[C:8]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([N:34]2[CH2:33][CH2:32][C:25]3([O:24][C:23](=[O:37])[NH:22][C:27]4[N:28]=[CH:29][CH:30]=[CH:31][C:26]3=4)[CH2:36][CH2:35]2)[CH:7]=1)=[O:9]

Participants

Conditions

Temperature: 130 °C

Procedure

0.23 g (0.78 mmol) (2-chloro-pyridin-4-yl)-(4,5-difluoro-2,3-dihydro-indol-1-yl)-methanone were added to 0.20 g (0.78 mmol) spiro[piperidine-4,4′-pyrido[2,3-d][1,3]oxazin]-2′(1′H)-one-hydrochloride and 0.11 g (0.78 mmol) potassium carbonate in 3.0 mL NMP. The reaction mixture was first of all stirred for 10 h at 130° C., then cooled to RT and then stirred overnight at RT. The crude product was combined with water/acetonitrile and purified by preparative HPLC-MS. The product fractions were combined and evaporated down. The residue was triturated with diisopropylether, suction filtered and dried in the air.

Workup

temperaturecooled to RT
stirringstirred overnight at RT
custompurified by preparative HPLC-MS
customevaporated down
customThe residue was triturated with diisopropylether, suction
filtrationfiltered
customdried in the air

Sources & evidence

ORD record: ord-2018704cc1174aaa8ca8deffb705e67d
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08110575B2

Reaction notes

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