Methoxyacetyl chloride → HCID 66780537, compound

HRID 1958035Notes

Reaction equation

HRID 1958035 reaction equation
[Cl:1][C:2]1[C:3]([CH3:24])=[C:4]([CH2:8][NH:9][C:10]2[N:11]=[C:12]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[S:13][C:14]=2[C:15]([NH2:17])=[O:16])[CH:5]=[CH:6][CH:7]=1.[CH3:25][O:26][CH2:27][C:28](Cl)=O>O1CCCC1>[Cl:1][C:2]1[C:3]([CH3:24])=[C:4]([CH2:8][N:9]2[C:10]3[N:11]=[C:12]([N:18]4[CH2:19][CH2:20][O:21][CH2:22][CH2:23]4)[S:13][C:14]=3[C:15](=[O:16])[N:17]=[C:28]2[CH2:27][O:26][CH3:25])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 96623Methoxyacetyl chlorideHCID 66779830HCID 66779830, compound

Product 1

HCID 66780537HCID 66780537, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-{[(3-chloro-2-methylphenyl)methyl]amino}-2-(4-morpholinyl)-1,3-thiazole-5-carboxamide (100 mg, 0.273 mmol) in Tetrahydrofuran (THF) (8001) at 0° C. was added methoxyacetyl chloride (49.7 μl, 0.545 mmol). The mixture was stirred at room temperature overnight, then quenched with methanol and concentrated. The residue was purified by reversed-phase HPLC to provide 4-[(3-chloro-2-methylphenyl)methyl]-5-[(methyloxy)methyl]-2-(4-morpholinyl)[1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one. (16 mg, 14%); LC/MS: MS (ES+) m/e 421 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.43 (s, 3H), 3.23 (s, 3H), 3.49-3.54 (m, 4H), 3.57-3.65 (m, 4H), 4.36 (s, 2H), 5.54 (s, 2H), 6.54 (d, J=7.6 Hz, 1H), 7.14 (m, 1H), 7.37 (d, J=7.8 Hz, 1H).

Workup

  1. customquenched with methanol
  2. concentrationconcentrated
  3. customThe residue was purified by reversed-phase HPLC

Sources & evidence

ORD record
ord-0af2a013ea084444b9ccd5d1c202192a
Source dataset
uspto-grants-2013_04
Patent number
US08410095B2

Reaction notes

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