N-methyl-2-pyrrolidone → N-[2-(4-amino-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl)ethyl]-3-chloropropane-1-sulfonamide

HRID 2283905Notes

Reaction equation

HRID 2283905 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[N:5]([CH2:18][CH2:19][CH3:20])[N:6]=[C:7]2[C:16]=1[C:15]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:9]=[C:8]2[NH2:17].C(N(CC)C(C)C)(C)C.[Cl:30][CH2:31][CH2:32][CH2:33][S:34](Cl)(=[O:36])=[O:35].CN1CCCC1=O>C(Cl)(Cl)Cl>[NH2:17][C:8]1[C:7]2=[N:6][N:5]([CH2:18][CH2:19][CH3:20])[C:4]([CH2:3][CH2:2][NH:1][S:34]([CH2:33][CH2:32][CH2:31][Cl:30])(=[O:36])=[O:35])=[C:16]2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:9]=1

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 154103-Chloropropanesulphonyl chlorideHCID 81531DiisopropylethylamineHCID 669583921-(2-aminoethyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-amine

Product 1

HCID 66958452N-[2-(4-amino-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl)ethyl]-3-chloropropane-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Under a nitrogen atmosphere, a solution of 1-(2-aminoethyl)-2-propyl-2H-pyrazolo[3,4-c]quinolin-4-amine (0.228 g, 0.848 mmol) and N,N-diisopropylethylamine (0.604 mL, 3.39 mmol) in chloroform (6.67 mL) was cooled to 0° C. A solution of 3-chloropropanesulfonyl chloride (0.113 mL, 0.933 mmol) in chloroform (10 mL) was added. An analysis by HPLC indicated that the reaction was not progressing. N-Methylpyrrolidone (12 mL) was added, and the reaction went to completion. The solvents were removed under reduced pressure to provide N-[2-(4-amino-2-propyl-2H-pyrazolo[3,4-c]quinolin-1-yl)ethyl]-3-chloropropane-1-sulfonamide.

Workup

  1. customThe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-f5ed9feeaecc4a27b931e37ec2233dcc
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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