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Hydrochloric Acid → [4-Azidomethyl-1-hydroxy-6-(pyrazin-2-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester

HRID 1798254
Notes
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Reaction equation

HRID 1798254 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([OH:20])[CH:14]=[C:15]([CH2:16][N:17]=[N+:18]=[N-:19])[C:7]1=2)[CH3:2].Cl[C:23]1[CH:28]=[N:27][CH:26]=[CH:25][N:24]=1.C([O-])([O-])=O.[Cs+].[Cs+].Cl>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:20][C:23]3[CH:28]=[N:27][CH:26]=[CH:25][N:24]=3)[CH:14]=[C:15]([CH2:16][N:17]=[N+:18]=[N-:19])[C:7]1=2)[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 73277ChloropyrazineHCID 58292573(4-Azidomethyl-1,6-dihydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester

Product 1

HCID 58292690[4-Azidomethyl-1-hydroxy-6-(pyrazin-2-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl esterYield 28.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of (4-azidomethyl-1,6-dihydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (550 mg, 1.89 mmol), 2-chloropyrazine (350 mg, 3.05 mmol), Cs2CO3 (1.34 g, 4.11 mmol) in 5 mL of DMF was heated to 80° C. for 3.5 h. The reaction mixture was adjusted to pH 3 by 1N HCl. The crude product was purified by HPLC to yield 200 mg of the title compound.

Workup

  1. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-e18e0ca404aa4da085de118aed22fe98
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08343944B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes