Cesium carbonate → HCID 11683683, compound

HRID 917429Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][N:27]=1)[C:5]([NH:7][C:8]1[S:9][C:10]2[C:11]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[N:12][CH:13]=[C:14]([O:17][CH3:18])[C:15]=2[N:16]=1)=[O:6].Cl.[NH:29]1[CH2:32][CH:31]([OH:33])[CH2:30]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1CCCC1=O>[OH:33][CH:31]1[CH2:32][N:29]([C:2]2[CH:3]=[C:4]([CH:25]=[CH:26][N:27]=2)[C:5]([NH:7][C:8]2[S:9][C:10]3[C:11]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[N:12][CH:13]=[C:14]([O:17][CH3:18])[C:15]=3[N:16]=2)=[O:6])[CH2:30]1

Participants

Conditions

Temperature: 150 °C

Procedure

A stirred suspension of 200 mg (0.44 mmol) 2-bromo-N-(7-methoxy-4-morpholin-4-yl-thiazolo[5,4-c]pyridin-2-yl)-isonicotinamide, 487 mg (4.44 mmol) azetidin-3-ol hydrochloride and 2.17 g (6.66 mmol) cesium carbonate in 6 ml N-methyl-pyrrolidone in a thick-walled glass pressure tube fitted with a teflon cap was heated at 150° C. for 6 h. The reaction mixture was then cooled to room temperature and partitioned between ethyl acetate and brine. The organic phase was dried over sodium sulfate and concentrated in vacuo. Flash chromatography (methanol/dichloromethane) followed by trituration in ether afforded 29 mg (15%) 2-(3-hydroxy-azetidin-1-yl)-N-(7-methoxy-4-morpholin-4-yl-thiazolo[5,4-c]pyridin-2-yl)-isonicotinamide as a brown crystalline solid. ES-MS m/e (%): 443 (M+H+, 100).

Workup

customcap
temperatureThe reaction mixture was then cooled to room temperature
custompartitioned between ethyl acetate and brine
dry with materialThe organic phase was dried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-ab8c1961913547e0852ab892348b0ac1
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07273865B2

Reaction notes

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