2-(Methylsulfanyl)acetyl chloride → HCID 178518229, compound

HRID 1958042Notes

Reaction equation

HRID 1958042 reaction equation
ClC1C(C)=C([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])C=CC=1.CSCC(Cl)=O>COCCOC>[N:18]1([C:12]2[S:13][C:14]3[C:15](=[O:16])[N:17]=[CH:8][NH:9][C:10]=3[N:11]=2)[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 111262562-(Methylsulfanyl)acetyl chlorideHCID 66779830HCID 66779830, compound

Product 1

HCID 178518229HCID 178518229, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

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 1,2-Dimethoxyethane (DME) (1000 μl) was added (methylthio)acetyl chloride (67.9 mg, 0.545 mmol) in 1,2-Dimethoxyethane (DME) (400 μl). The mixture was stirred at room temperature for 3 h, then irradiated (uwave) at 90° C. for 15 min. After quenching with methanol, the mixture was concentrated and purified by reversed-phase HPLC to provide 4-[(3-chloro-2-methylphenyl)methyl]-5-[(methylthio)methylthio)methyl]-2-(4-morpholinyl)[1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one. (28 mg, 24%); LC/MS: MS (ES+) m/e 437 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.11 (s, 3H), 2.43 (s, 3H), 3.51 (m, 4H), 3.62 (s, 2H), 3.64-3.71 (m, 4H), 5.59 (s, 2H), 6.53 (d, J=7.8 Hz, 1H), 7.15 (m, 1H), 7.38 (d, J=8.01 Hz, 1H).

Workup

  1. customirradiated (uwave) at 90° C. for 15 min
  2. customAfter quenching with methanol
  3. concentrationthe mixture was concentrated
  4. custompurified by reversed-phase HPLC

Sources & evidence

ORD record
ord-5ec648e9312945b997bfe1e68e5181b8
Source dataset
uspto-grants-2013_04
Patent number
US08410095B2

Reaction notes

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