Pyridine → HCID 59791329, compound

A solution of [5-(3-chloropropyl)-2-furyl]methanol (500 mg, 2.5 mmol) in ether (6 mL) was dried over 3 {acute over (Å)} molecular sieves. After the sieves were removed, pyridine (245 μL, 3.0 mmol) was added to the solution. Thionyl bromide (215 μL, 2.9 mmol) was added dropwise to the solution. After 7 hours of stirring, the solution was rapidly injected into a solution of sodium 2-[2-aminoethoxy]ethoxide (534 mg, 4.2 mmol) in DMF (3 mL). (Sodium 2-[2-aminoethoxy]ethoxide was previously prepared by adding 60% NaH dispersion (2.85 g, 0.07 mol) subsequently cleaned with heptane to a solution of 2-aminoethoxyethanol (5 g, 0.04 mol) in diglyme (10 mL), stirred for 5 hours, and evaporated.) After 2 hours the reaction was placed in the freezer. After 18 hours the reaction was partitioned between dichloromethane (DCM) (50 mL) and water (50 mL). Water layer was extracted with additional 30 mL DCM. The combined DCM layers were washed with water (30 mL). The DCM layer were extracted with diluted HCl (1N, 30 mL) followed by water (20 mL). The acidic aqueous solutions were adjusted to pH=10 with diluted sodium hydroxide and back extracted with 2×20 ml DCM. The DCM was washed with brine, dried with sodium sulfate, filtered, and evaporated to yield 380 mg (58% yield). Used without further purification. TLC: Rf 0.5 (IPA/NH4OH/water 8/1/1 exposed with ninhydrin solution) Mass spectrum, m/e Calcd for C12H21ClNO3+: 262.1 (100%), 264.1 (32%). Found: 262.6, 264.6.

1. customAfter the sieves were removed
2. stirringstirred for 5 hours
3. customevaporated
4. wait) After 2 hours the reaction was placed in the freezer
5. customAfter 18 hours the reaction was partitioned between dichloromethane (DCM) (50 mL) and water (50 mL)
6. extractionWater layer was extracted with additional 30 mL DCM
7. washThe combined DCM layers were washed with water (30 mL)
8. extractionThe DCM layer were extracted with diluted HCl (1N, 30 mL)
9. extractionback extracted with 2×20 ml DCM
10. washThe DCM was washed with brine
11. dry with materialdried with sodium sulfate
12. filtrationfiltered
13. customevaporated
14. customto yield 380 mg (58% yield)
15. customUsed without further purification

ORD record

ord-e3362a4abb1044a7babc935a615c731b

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09416353B2