Acetoxyacetyl chloride → HCID 66780137, compound

HRID 1958037Notes

Reaction equation

HRID 1958037 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.[C:25]([O:28][CH2:29][C:30](Cl)=O)(=[O:27])[CH3:26]>O1CCCC1>[C:25]([O:28][CH2:29][C:30]1[N:9]([CH2:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=2[CH3:24])[C:10]2[N:11]=[C:12]([N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)[S:13][C:14]=2[C:15](=[O:16])[N:17]=1)(=[O:27])[CH3:26]

Participants

4

Reactant 2

HCID 26297Acetoxyacetyl chlorideHCID 66779830HCID 66779830, compound

Product 1

HCID 66780137HCID 66780137, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-{[(3-chloro-2-methylphenyl)methyl]amino}-2-(4-morpholinyl)-1,3-thiazole-5-carboxamide (200 mg, 0.545 mmol) in Tetrahydrofuran (THF) (2726 μl) at 0° C. was added acetoxyacetyl chloride (117 μl, 1.090 mmol). The mixture was stirred at 50° C. for 3 h, then quenched with methanol and concentrated. The residue was subjected to silica gel chromatography (0-5% methanol/dichloromethane) followed by reversed-phase HPLC purification to provide [4-[(3-chloro-2-methylphenyl)methyl]-2-(4-morpholinyl)-7-oxo-4,7-dihydro[1,3]thiazolo[4,5-d]pyrimidin-5-yl]methyl acetate. (49 mg, 20%); LC/MS: MS (ES+) m/e 449 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.85 (s, 3H), 2.42 (s, 3H), 3.52 (m, 4H), 3.67 (m, 4H), 5.03 (s, 2H), 5.50 (s, 2H), 6.54 (d, J=7.6 Hz, 1H), 7.17 (m, 1H), 7.39 (d, J=7.8 Hz, 1H).

Workup

  1. customquenched with methanol
  2. concentrationconcentrated
  3. customfollowed by reversed-phase HPLC purification

Sources & evidence

ORD record
ord-2228d4cc48ac4d1a8f218a42aca87d11
Source dataset
uspto-grants-2013_04
Patent number
US08410095B2

Reaction notes

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