1190927-27-5 → HCID 57464053, compound

HRID 547358Notes

Reaction equation

HRID 547358 reaction equation
[C:1]([N:4]1[CH2:9][C@@H:8]2[CH2:10][C@H:5]1[CH2:6][N:7]2[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O-:18])=[CH:14][CH:13]=1)(=[O:3])[CH3:2].[Na+].Cl[C:21]1[S:22][C:23]2[C:28]([N:29]=1)=[CH:27][CH:26]=[C:25]([CH3:30])[N:24]=2>CN(C=O)C>[C:1]([N:4]1[CH2:9][C@@H:8]2[CH2:10][C@H:5]1[CH2:6][N:7]2[CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][C:21]2[S:22][C:23]3[C:28]([N:29]=2)=[CH:27][CH:26]=[C:25]([CH3:30])[N:24]=3)=[CH:16][CH:17]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 574483771190927-27-5HCID 57514844HCID 57514844, compound

Product 1

HCID 57464053HCID 57464053, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To sodium 4-{[(1S,4S)-5-acetyl-2,5-diazabicyclo[2.2.1]hept-2-yl]methyl}phenolate (170 mg, 0.63 mmol) was added 2-chloro-5-methyl[1,3]thiazolo[5,4-b]pyridine (117 mg, 0.63 mmol) and DMF (6.3 mL). The solution was stirred for 16 h, filtered, and purified by preparative reverse phase HPLC to provide the desired product (140 mg, 56%). 1H NMR (400 MHz, CDCl3): 7.81 (d, J=8.2, 1H), 7.46-7.39 (m, 2H), 7.33-7.28 (m, 2H), 7.18 (d, J=8.3, 1H), 4.79 (s, 0.5H), 4.24 (s, 0.5H), 3.82-3.72 (m, 2.5H), 3.60-3.53 (m, 1.5H), 3.30 (ddd, J=13.3, 10.3, 2.1, 1H), 3.02 (dd, J=9.5, 2.1, 0.5H), 2.85 (dd, J=9.7, 2.2, 0.5H), 2.78 (d, J=9.7, 0.5H), 2.61 (s, 3H), 2.57 (dd, J=9.5, 1.2, 0.5H), 2.08 (s, 1.5H), 2.03-1.96 (m, 2H), 1.91 (d, J=9.8, 0.5H), 1.81 (d, J=9.7, 0.5H), 1.67 (d, J=10.0, 0.5H). MS (ESI): mass calcd. for C21H22N4O2S, 394.15; m/z found, 395.1 [M+H]+.

Workup

  1. filtrationfiltered
  2. custompurified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-e26530975b7c45f9ab2590f3a4828361
Source dataset
uspto-grants-2011_05
Patent number
US07939527B2

Reaction notes

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