Sodium Bicarbonate → HCID 67294907, compound

HRID 589162Notes

Reaction equation

C[Si](C)(C)CCOC[N:7](COCC[Si](C)(C)C)[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:21][CH:22]=3)=[C:12]2[N:11]=[C:10]([CH:29]2[CH2:35][CH:34]3[N:36]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH:31]([CH2:32][CH2:33]3)[CH2:30]2)[C:9]=1SC.O[O:57][S:58]([O-:60])=O.[K+].[C:62]([O-])(O)=O.[Na+]>CO.O>[NH2:7][C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)=[CH:21][CH:22]=3)=[C:12]2[N:11]=[C:10]([CH:29]2[CH2:30][CH:31]3[N:36]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH:34]([CH2:33][CH2:32]3)[CH2:35]2)[C:9]=1[S:58]([CH3:62])(=[O:60])=[O:57]

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of compound tert-butyl 3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-(methylthio)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-8-azabicyclo[3.2.1]octane-8-carboxylate (319 mg, 0.4 mmol), Oxone (1.2 g, 2 mmol) and NaHCO3 (336 mg, 4 mmol) in MeOH (12 mL) and Water (3 mL) was heated at 65° C. for 15 h, at which time LC/MS analysis confirmed full consumption of starting material. After cooling, it was diluted with DCM: MeOH (1:1, 100 mL) and filtered. The filtrate was concentrated to afford the crude title product which was used for the next step without further purification.

Workup

customconsumption of starting material
temperatureAfter cooling
additionit was diluted with DCM: MeOH (1:1, 100 mL)
filtrationfiltered
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-3ce7861ddfde462497557450db43252a
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227971B2

Reaction notes

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