Phenoxyacetyl chloride → HCID 66780191, compound

HRID 1958038Notes

Reaction equation

HRID 1958038 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:12][NH:13][C:14]1[N:15]=[C:16]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[S:17][C:18]=1[C:19]([NH2:21])=[O:20].[O:28]([CH2:35][C:36](Cl)=O)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O1CCCC1>[CH3:1][C:2]1[C:7]([C:8]([F:9])([F:10])[F:11])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:12][N:13]1[C:14]2[N:15]=[C:16]([N:22]3[CH2:23][CH2:24][O:25][CH2:26][CH2:27]3)[S:17][C:18]=2[C:19](=[O:20])[N:21]=[C:36]1[CH2:35][O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 69703Phenoxyacetyl chlorideHCID 66779840HCID 66779840, compound

Product 1

HCID 66780191HCID 66780191, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-({[2-methyl-3-(trifluoromethyl)phenyl]methyl}amino)-2-(4-morpholinyl)-1,3-thiazole-5-carboxamide (100 mg, 0.250 mmol) in Tetrahydrofuran (THF) (1249 μl) at 0° C. was added phenoxyacetyl chloride (69.0 μl, 0.499 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-{([2-methyl-3-(trifluoromethyl)phenyl]methyl}-2-(4-morpholinyl)-5-[(phenyloxy)methyl][1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one. (14 mg, 11%); LC/MS: MS (ES+) m/e 517 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.34 (s, 3H), 3.48-3.54 (m, 4H), 3.62-3.71 (m, 4H), 5.12 (s, 2H), 5.57 (s, 2H), 6.61 (d, J=7.8 Hz, 2H), 6.85-6.97 (m, 2H), 7.19 (dd, J=8.7, 7.5 Hz, 2H), 7.25-7.33 (m, 1H), 7.60 (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-f05517381daf489a8a638cc8e15f07b9
Source dataset
uspto-grants-2013_04
Patent number
US08410095B2

Reaction notes

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