Dimethylamine → HCID 58292687, compound

HRID 1798195Notes

Reaction equation

HRID 1798195 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:17][C:18]3[CH:23]=[CH:22][N:21]=[C:20](Cl)[N:19]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)[CH3:2].[CH3:26][NH:27][CH3:28]>>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([O:17][C:18]3[CH:23]=[CH:22][N:21]=[C:20]([N:27]([CH3:28])[CH3:26])[N:19]=3)[CH:14]=[C:15]([CH3:16])[C:7]1=2)[CH3:2]

Participants

3

Reactant 2

HCID 674DimethylamineHCID 58292555HCID 58292555, compound

Product 1

HCID 58292687HCID 58292687, compoundYield 22%

Procedure

A solution of [6-(2-chloro-pyrimidin-4-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (impure, 0.42 g, 1.16 mmol) in dimethylamine (2M solution in THF, 5 mL, 10 mmol) was stirred in a sealed tube at room temperature for 3 hours. The mixture was concentrated in vacuo and the residue purified by silica gel flash column chromatography using EtOAc and hexane (1:1) as eluant, followed by MeOH and CH2Cl2 (2:98 gradient) and preparative HPLC (CH3CN/0.1% AcOH in water). The required fraction was lyophilized to give [6-(2-dimethylamino-pyrimidin-4-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester as a light yellow solid (0.094 g, 22%). 1H NMR (400 MHz, CD3OD) δ8.12 (d, J=5.85 Hz, 1H), 7.19 (s, 1H), 7.05 (s, 1H), 6.07 (d, J=5.85 Hz, 1H), 5.68-5.60 (m, 1H), 4.15-4.03 (m, 2H), 3.17 (dd, J=14.38, 2.34 Hz, 1H), 3.00 (s, 6H), 2.47 (dd, J=14.83, 8.20 Hz, 1H), 2.36 (s, 3H), 1.20 (t, J=7.03 Hz, 3H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-4f202f5be1f44d0495191525e2c0a62d
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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