Cesium carbonate → HCID 72714975, compound

HRID 1396515Notes

Reaction equation

C([O-])([O-])=O.[Cs+].[Cs+].[CH2:7]([O:14][C:15]1[CH:25]=[C:18]2[C:19](=[O:24])[NH:20][CH2:21][CH2:22][CH2:23][N:17]2[N:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Br[CH2:27][CH:28]1[CH2:30][CH2:29]1>CN(C=O)C>[CH2:7]([O:14][C:15]1[CH:25]=[C:18]2[C:19](=[O:24])[N:20]([CH2:27][CH:28]3[CH2:30][CH2:29]3)[CH2:21][CH2:22][CH2:23][N:17]2[N:16]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of Cs2CO3 (0.8 g, 2.43 mmol) in DMF (10 mL) were added 2-(benzyloxy)-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepin-4-one (0.3 g, 1.16 mmol) and (bromomethyl)cyclopropane (0.3 g, 2.34 mmol) at 0° C. The mixture was stirred at 150° C. for 18 hours. The mixture was diluted with ice-water and extracted with AcOEt. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in petroleum ether 0/10 to 1/10) to yield 2-(benzyloxy)-5-(cyclopropylmethyl)-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepin-4-one (97 mg, 27% yield). C18H21N3O2. 1H NMR (400 MHz, CDCl3) δ ppm 0.27-0.39 (m, 2H), 0.51-0.66 (m, 2H), 1.01-1.14 (m, 1H), 2.28 (quin, J=6.7 Hz, 2H), 3.43 (d, J=7.3 Hz, 2H), 3.48 (t, J=6.4 Hz, 2H), 4.28 (t, J=7.0 Hz, 2H), 5.18 (s, 2H), 6.18 (s, 1H), 7.28-7.40 (m, 3H), 7.41-7.47 (m, 2H).

Workup

extractionextracted with AcOEt
customThe organic layer was separated
dry with materialdried (Na2SO4)
filtrationfiltered
customthe solvents evaporated in vacuo
customThe crude product was purified by flash column chromatography (silica; AcOEt in petroleum ether 0/10 to 1/10)

Sources & evidence

ORD record: ord-a3841632e24d43979ccb802522e74f08
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901125B2

Reaction notes

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