TETRAHYDROPYRAN-2-CARBONYL CHLORIDE → HCID 66780356, compound

HRID 1958041Notes

Reaction equation

HRID 1958041 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]1[CH2:30][CH2:29][CH2:28][CH2:27][CH:26]1[C:31](Cl)=O>COCCOC>[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:31]2[CH:26]2[CH2:27][CH2:28][CH2:29][CH2:30][O:25]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 15731743TETRAHYDROPYRAN-2-CARBONYL CHLORIDEHCID 66779830HCID 66779830, compound

Product 1

HCID 66780356HCID 66780356, 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 ul) was added tetrahydro-2H-pyran-2-carbonyl chloride (81 mg, 0.545 mmol) in 1,2-Dimethoxyethane (DME) (400 ul). The mixture was stirred at room temperature for 3 h, then irradiated (uwave) for 20 min at 90° C. The mixture was quenched with methanol, concentrated, and purified by reversed-phase HPLC to provide 4-[(3-chloro-2-methylphenyl)methyl]-2-(4-morpholinyl)-5-(tetrahydro-2H-pyran-2-yl)[1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one. (17 mg, 14%); LC/MS: MS (ES*) m/e 461 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.46 (br. s., 3H), 1.62-1.72 (m, 1H), 1.78-1.98 (m, 2H), 2.45 (s, 3H), 3.45-3.57 (m, 5H), 3.66 (t, J=4.8 Hz, 4H), 3.81 (d, J=11.6 Hz, 1H), 4.28 (m, 1H), 5.51-5.66 (m, 2H), 6.49 (d, J=7.8 Hz, 1H), 7.13 (m, 1H), 7.36 (d, J=7.8 Hz, 1H).

Workup

  1. customirradiated (uwave) for 20 min at 90° C
  2. customThe mixture was quenched with methanol
  3. concentrationconcentrated
  4. custompurified by reversed-phase HPLC

Sources & evidence

ORD record
ord-42106acbb06b477885bc42f99c28a955
Source dataset
uspto-grants-2013_04
Patent number
US08410095B2

Reaction notes

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