Acetonitrile → HCID 44481312, compound

HRID 1807461Notes

Reaction equation

HRID 1807461 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[S:16][C:17]3[C:18]([N:23]=2)=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:10][CH:9]=1)(=O)=O.[C:24]([N:27]1[CH2:32][C@@H:31]2[CH2:33][C@H:28]1[CH2:29][NH:30]2)(=[O:26])C.C([O-])([O-])=O.[K+].[K+].CC#[N:42]>>[S:16]1[C:17]2[C:18](=[N:19][CH:20]=[CH:21][CH:22]=2)[N:23]=[C:15]1[O:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][CH2:6][N:30]2[CH2:29][C@@H:28]3[CH2:33][C@H:31]2[CH2:32][N:27]3[C:24]([NH2:42])=[O:26])=[CH:9][CH:10]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 55300725HCID 55300725, compoundHCID 57448382HCID 57448382, compound

Product 1

HCID 44481312HCID 44481312, compoundYield 16%

Conditions

Temperature
80 °C

Procedure

To a solution of 2-[4-([1,3]thiazolo[4,5-b]pyridin-2-yloxy)phenyl]ethyl methanesulfonate (100 mg, 0.29 mmol, 1.0 equiv.) and (1 S,4S)-2-acetyl-2,5-diazabicyclo[2.2.1]heptane (48 mg, 0.34 mmol, 1.2 equiv.) in CH3CN (3 mL) was added K2CO3 (39 mg, 0.29 mmol, 1.0 equiv.). The solution was stirred at 80° C. for 16 h and then cooled to rt. Purification by preparative reverse phase HPLC produced a white solid (16%). 1H NMR (500 MHz, CDCl3): 8.57 (dd, J=4.8, 1.7, 1H), 8.03 (dd, J=7.9, 1.7, 1H), 7.36-7.28 (m, 4H), 7.22 (dd, J=7.9, 4.8, 1H), 4.32 (s, 2H), 3.61 (s, 1H), 3.23 (dd, J=8.8, 2.1, 1H), 3.02 (dd, J=9.5, 2.0, 1H), 3.53-3.46 (m, 1H), 2.90-2.77 (m, 4H), 2.73 (d, J=9.4, 1H), 1.92 (d, J=9.6, 1H), 1.77 (d, J=9.3, 1H), 1.62 (s, 1H). MS (ESI): mass calcd. for C20H21N6O2S, 395.14; m/z found, 396.1 [M+H]+.

Workup

  1. temperaturecooled to rt
  2. customPurification by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-0d2554e135f64c46b095b9c6ffde5633
Source dataset
uspto-grants-2013_01
Patent number
US08357684B2

Reaction notes

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