(1S)-2-Chloro-1-methyl-2-oxoethyl acetate → HCID 66780637, compound

HRID 1958039Notes

Reaction equation

HRID 1958039 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][C@@H:29]([CH3:33])[C:30](Cl)=O)(=[O:27])[CH3:26]>O1CCCC1>[C:25]([O:28][C@H:29]([C:33]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)[CH3:30])(=[O:27])[CH3:26]

Participants

4

Reactant 2

HCID 11094804(1S)-2-Chloro-1-methyl-2-oxoethyl acetate2×HCID 66779830HCID 66779830, compound

Product 1

HCID 66780637HCID 66780637, 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) (1363 μl) was added (1S)-2-chloro-1-methyl-2-oxoethyl acetate (82 mg, 0.545 mmol). The mixture was stirred at room temperature overnight, then additional (1S)-2-chloro-1-methyl-2-oxoethyl acetate (1 equiv.) was added and stirring was continued at 60° C. for 2 h. The mixture was quenched with methanol and concentrated. The residue was purified by reversed-phase HPLC to provide (1S)-1-[4-[(3-chloro-2-methylphenyl)methyl]-2-(4-morpholinyl)-7-oxo-4,7-dihydro[1,3]thiazolo[4,5-d]pyrimidin-5-yl]ethyl acetate. (11 mg, 9%); LC/MS: MS (ES+) m/e 463 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.37 (d, J=6.3 Hz, 3H), 1.71 (s, 3H), 2.40 (s, 3H), 3.51-3.54 (m, 4H), 3.67 (m, 4H), 5.48-5.61 (m, 2H), 5.69 (q, J=6.3 Hz, 1H), 6.56 (d, J=7.6 Hz, 1H), 7.16 (m, 1H), 7.38 (d, J=7.8 Hz, 1H).

Workup

  1. stirringstirring
  2. waitwas continued at 60° C. for 2 h
  3. customThe mixture was quenched with methanol
  4. concentrationconcentrated
  5. customThe residue was purified by reversed-phase HPLC

Sources & evidence

ORD record
ord-ac476d7ced8341ab823aebe4bfbf5897
Source dataset
uspto-grants-2013_04
Patent number
US08410095B2

Reaction notes

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