4-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl)morpholine → 5-(5-methoxy-1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine

HRID 1851771Notes

Reaction equation

HRID 1851771 reaction equation
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9](OC)[CH:8]=[CH:7][C:5]=2[N:6]=1.CC1(C)C(C)(C)OB([C:21]2[CH:22]=[CH:23][C:24]([N:27]3CCOC[CH2:28]3)=[N:25][CH:26]=2)O1.[CH3:34][O:35]C1C=CC2N=C(C3C=NC(N)=NC=3)SC=2C=1>>[CH3:34][O:35][C:8]1[CH:9]=[CH:10][C:4]2[S:3][C:2]([C:21]3[CH:22]=[CH:23][C:24]([NH:27][CH3:28])=[N:25][CH:26]=3)=[N:6][C:5]=2[CH:7]=1

Participants

4

Reactant 3

HCID 27953634-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl)morpholineHCID 112187652-Bromo-6-methoxy-1,3-benzothiazoleHCID 248040695-(6-Methoxy-1,3-benzothiazol-2-yl)pyrimidin-2-amine

Product 1

HCID 248037275-(5-methoxy-1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine

Procedure

2-Bromo-6-methoxy-1,3-benzothiazole (49 mg, 0.20 mmol), 4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]morpholine (70 mg, 0.24 mmol) were reacted according to the procedure used for the preparation of 5-(6-methoxy-1,3-benzothiazol-2-yl)pyrimidin-2-amine, with the following exceptions: The reaction was heated for 4 h before the solvent was evaporated under reduced pressure. The residue was dissolved in MeOH/DCM 1:1 and filtered through silica. The filtrate was concentrated and the crude product was purified by preparative HPLC to give the title compound (0.6 mg). 1H NMR (CHLOROFORM-d) δ 8.79 (d, 1 H) 8.18 (dd, 1 H) 7.90 (d, 1 H) 7.35 (d, 1 H) 7.08 (dd, 1 H) 6.71 (d, 1 H) 3.90 (s, 3 H) 3.87-3.83 (m, 4 H) 3.67-3.63 (m, 4 H); MS m/z (M+H) 328.

Workup

  1. temperatureThe reaction was heated for 4 h before the solvent
  2. customwas evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in MeOH/DCM 1:1
  4. filtrationfiltered through silica
  5. concentrationThe filtrate was concentrated
  6. customthe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-51323ea058914853805a390e56a1879e
Source dataset
uspto-grants-2015_02
Patent number
US08957215B2

Reaction notes

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