Triethylamine → HCID 178490650, compound

HRID 1028185Notes

Reaction equation

HRID 1028185 reaction equation
[N:1]1[C:5]2[CH2:6][CH2:7][O:8][CH2:9][C:4]=2[S:3][C:2]=1[NH2:10].[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([O:21][CH3:22])=[C:16]([CH:20]=1)[C:17](O)=[O:18].ON1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C>O1CCCC1.CN(C)C=O.CCOC(C)=O>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([O:21][CH3:22])=[C:16]([CH:20]=1)[C:17](/[N:10]=[C:2]1\[S:3][C:4]2[CH2:9][O:8][CH2:7][CH2:6][C:5]=2[NH:1]\1)=[O:18]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 769705-Chloro-o-anisic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 222244484H,6H,7H-pyrano(4,3-d)(1,3)thiazol-2-amine

Product 1

HCID 178490650HCID 178490650, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of commercially available 6,7-dihydro-4H-pyrano[4,3-d]thiazol-2-amine (1.73 g, 11.1 mmol, JW-Pharmalab) in tetrahydrofuran/N,N-dimethylformamide (5:1, 60 mL) were added 5-chloro-2-methoxybenzoic acid (2.27 g, 12.2 mmol, Aldrich), 1-hydroxybenzotriazole (1.9 g, 12.2 mmol, Aldrich), N-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride (2.3 g, 12.2 mmol, Aldrich) and triethylamine (4.6 ml, 33.2 mmol). After stirring at 60° C. for 16 h, the reaction mixture was cooled, diluted with EtOAc (50 mL) and quenched with saturated NaHCO3 (50 mL). The aqueous layer was extracted with EtOAc (2×50 mL). The combined organic extracts were washed with brine (50 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by column chromatography using an Analogix® Intelliflash280 ™ (SiO2, 0-5% methanol in methylene chloride). MS (ESI+) m/z 325 (M+H)+.

Workup

  1. temperaturethe reaction mixture was cooled
  2. customquenched with saturated NaHCO3 (50 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (2×50 mL)
  4. washThe combined organic extracts were washed with brine (50 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-bde2bd615af040ed91e835f5b7e4e135
Source dataset
uspto-grants-2014_05
Patent number
US08735434B2

Reaction notes

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