Potassium Carbonate → HCID 68312908, compound

HRID 1530563Notes

Reaction equation

[CH3:1][CH:2]([N:4]1[C:8]([C:9]2[N:10]=[C:11]3[N:21]([CH:22]=2)[CH2:20][CH2:19][O:18][C:17]2[C:12]3=[CH:13][C:14]([CH:23]([CH2:25]S([O-])(=O)=O)C)=[CH:15][CH:16]=2)=[N:7][CH:6]=[N:5]1)[CH3:3].C([O-])([O-])=O.[K+].[K+].[NH:36]1[CH2:39][CH:38]([OH:40])[CH2:37]1>CC#N>[CH3:1][CH:2]([N:4]1[C:8]([C:9]2[N:10]=[C:11]3[N:21]([CH:22]=2)[CH2:20][CH2:19][O:18][C:17]2[C:12]3=[CH:13][C:14]([CH:23]([N:36]3[CH2:39][CH:38]([OH:40])[CH2:37]3)[CH3:25])=[CH:15][CH:16]=2)=[N:7][CH:6]=[N:5]1)[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1-{4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaen-13-yl}ethylmethanesulfonate (0.19 mmol, 80 mg) in CH3CN (10 mL) was added K2CO3 (0.72 mmol, 106 mg) and azetidin-3-ol (0.38 mmol, 28 mg), the mixture was stirred at 80° C. for 16 h. After concentration, the residue was purified by reverse phase Combiflash eluting with a 0-50% gradient of CH3CN in 0.3% NH4HCO3 to give 1-(1-{4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaen-13-yl}ethyl)azetidin-3-ol (70 mg, 92% yield). LCMS (ESI) m/z: 395.1 [M+H+]

Workup

concentrationAfter concentration
customthe residue was purified by reverse phase Combiflash
washeluting with a 0-50% gradient of CH3CN in 0.3% NH4HCO3

Sources & evidence

ORD record: ord-132720f8d75941f4a701a36ee25fa842
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090628B2

Reaction notes

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