Water → tert-Butyl 3-(8-morpholinoimidazo[1,2-a]pyrazin-2-yl)azetidine-1-carboxylate

HRID 1772651Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]([NH2:13])=[N:9][CH:10]=[CH:11][N:12]=2)[CH2:3][CH2:2]1.Br[CH2:15][C:16]([CH:18]1[CH2:21][N:20]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:19]1)=O.O>CN(C=O)C>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([CH:15]=[C:16]([CH:18]4[CH2:21][N:20]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:19]4)[N:13]=3)[CH:10]=[CH:11][N:12]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of compound 1b (2.4 g, 13 mmol) in DMF (20 mL), Na2HPO4 (4.7 g, 33 mmol) was added followed by tert-butyl 3-(2-bromoacetyl)azetidine-1-carboxylate (6.0, 21 mmol). The resulting mixture was stirred at 100° C. for 3 h. The reaction mixture was allowed to cool to rt and water (50 mL) was added. The aqueous layer was extracted with EtOAc (3×25 mL). The combined EtOAc layers were dried over Na2SO4, filtered, and concentrated. The residue obtained was purified by flash column chromatography on silica gel (0:1-1:0 EtOAc/hexanes) to obtain compound 29a. Mass Spectrum (LCMS, ESI pos.): Calcd. for C18H25N5O3: 360.2 (M+H). found: 360.3.

Workup

temperatureto cool to rt
extractionThe aqueous layer was extracted with EtOAc (3×25 mL)
dry with materialThe combined EtOAc layers were dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue obtained
customwas purified by flash column chromatography on silica gel (0:1-1:0 EtOAc/hexanes)

Sources & evidence

ORD record: ord-5c2296f817d9471799c82afa97af3fe7
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249163B2

Reaction notes

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