Phenoxyacetyl chloride → HCID 66780114, compound

HRID 1958036Notes

Reaction equation

HRID 1958036 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.[O:25]([CH2:32][C:33](Cl)=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>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:33]2[CH2:32][O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 69703Phenoxyacetyl chlorideHCID 66779830HCID 66779830, compound

Product 1

HCID 66780114HCID 66780114, 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) at 0° C. was added phenoxyacetyl chloride (75 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]-2-(4-morpholinyl)-5-[(phenyloxy)methyl][1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one. (19 mg, 14%); LC/MS: MS (ES+) m/e 483 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.29 (s, 3H), 3.52 (t, J=4.7 Hz, 4H), 3.67 (t, J=4.7 Hz, 4H), 5.07 (s, 2H), 5.55 (s, 2H), 6.55 (m, 1H), 6.69 (d, J=7.8 Hz, 2H), 6.94 (m, 1H), 7.12 (m, 1H), 7.22 (m, 2H), 7.36 (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-5dc5e081b0bd478da0cf3123b211ebbb
Source dataset
uspto-grants-2013_04
Patent number
US08410095B2

Reaction notes

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