Dimethylsulphamoyl chloride → HCID 69289960, compound

229.4 mg (1 mmol) of 2-methyl-4-pyrrolidin-1-yl-quinolin-7-ol, product of example 2, were suspended under an argon atmosphere in 20 ml of DMF, 0.6 g (1.2 mmol) of molecular sieves (4 nm) were added followed by 138 mg (1.2 mmol) of potassium tert-butoxide, and the mixture was stirred for 1 h at RT. It was then cooled to 0° C., treated with 0.13 ml (1.2 mmol) N,N-dimethylsulfamoyl chloride and stirred for 3 h at 0° C. The reaction mixture was partitioned between EtOAc and water, the aqueous layer was extracted twice with EtOAc, the combined organic layers were washed with water then with saturated NaCl solution, dried over magnesium sulphate and concentrated in vacuo. The residue was triturated with diethyl ether; the viscous oil obtained was filtered off by suction and dried in a high vacuum. Upon further triturating with heptane solid material was obtained which was dried in a high vacuum to give 100 mg (29.3%) of dimethyl-sulfamic acid 2-methyl-4-pyrrolidin-1-yl-quinolin-7-yl ester as an off-white solid. ISP mass spectrum, m/e: 336.2 (M+1 calculated for C16H21N3O3S: 336).

1. addition0.6 g (1.2 mmol) of molecular sieves (4 nm) were added
2. temperatureIt was then cooled to 0° C.
3. stirringstirred for 3 h at 0° C
4. customThe reaction mixture was partitioned between EtOAc and water
5. extractionthe aqueous layer was extracted twice with EtOAc
6. washthe combined organic layers were washed with water
7. dry with materialwith saturated NaCl solution, dried over magnesium sulphate
8. concentrationconcentrated in vacuo
9. customThe residue was triturated with diethyl ether
10. customthe viscous oil obtained
11. filtrationwas filtered off by suction
12. customdried in a high vacuum
13. customUpon further triturating with heptane solid material
14. customwas obtained which
15. customwas dried in a high vacuum

ORD record

ord-bae9839df2a640cfb2a79dde5af29d89

Source dataset

uspto-grants-2004_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06818767B2