Tetrahydro-2-furancarbonyl chloride → HCID 66780285, compound

HRID 1958032Notes

Reaction equation

HRID 1958032 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[CH2:29][CH2:28][CH2:27][CH:26]1[C:30](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:30]2[CH:26]2[CH2:27][CH2:28][CH2:29][O:25]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 551254Tetrahydro-2-furancarbonyl chloride2×HCID 66779830HCID 66779830, compound

Product 1

HCID 66780285HCID 66780285, 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 tetrahydro-2-furancarbonyl chloride (73.4 mg, 0.545 mmol) in 1,2-Dimethoxyethane (DME) (400 μl). The mixture was stirred at room temperature overnight, then additional tetrahydro-2-furancarbonyl chloride (1 equiv.) was added and the mixture was irradiated (uwave) for 15 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-2-furanyl)[1,3]thiazolo[4,5-d]pyrimidin-7(4H)-one. (18 mg, 15%); LC/MS: MS (ES+) m/e 447 (MH+); 1H NMR (400 MHz, DMSO-d6) δ ppm 1.79-1.91 (m, 1H), 1.94-2.05 (m, 2H), 2.35-2.42 (m, 1H), 2.43 (s, 3H), 3.55-3.60 (m, 4H), 3.67 (m, 4H), 3.76 m, 1H), 3.84 (qm, 1H), 4.79 (m, 1H), 5.64 (s, 2H), 6.52 (d, J=7.6 Hz, 1H), 7.14 (m, 1H), 7.37 (d, J=8.1 Hz, 1H).

Workup

  1. customthe mixture was irradiated (uwave) for 15 min at 90° C
  2. customThe mixture was quenched with methanol
  3. concentrationconcentrated
  4. custompurified by reversed-phase HPLC

Sources & evidence

ORD record
ord-5e86130c2658453687e8a4e3b2ecb27d
Source dataset
uspto-grants-2013_04
Patent number
US08410095B2

Reaction notes

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