p-(Methylsulphonyl)benzoic acid → 7-Chloro-3-[(4-methanesulfonyl-benzoylamino)-methyl]-4-oxo-1-phenyl-1,4-dihydro-quin-oline-2-carboxylic acid methyl ester

HRID 1887921Notes

Reaction equation

HRID 1887921 reaction equation
[CH3:1][S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.Cl.[CH3:39][O:40][C:41]([C:43]1[N:44]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[C:45]2[C:50]([C:51](=[O:55])[C:52]=1[CH2:53][NH2:54])=[CH:49][CH:48]=[C:47]([Cl:56])[CH:46]=2)=[O:42]>C(Cl)Cl>[CH3:39][O:40][C:41]([C:43]1[N:44]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[C:45]2[C:50]([C:51](=[O:55])[C:52]=1[CH2:53][NH:54][C:9](=[O:11])[C:8]1[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:13][CH:12]=1)=[CH:49][CH:48]=[C:47]([Cl:56])[CH:46]=2)=[O:42]

Participants

5

Reactant 3

HCID 77670p-(Methylsulphonyl)benzoic acidHCID 2733179PyBroPHCID 712085323-Aminomethyl-7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester hydrochloride2×

Product 1

HCID 712083777-Chloro-3-[(4-methanesulfonyl-benzoylamino)-methyl]-4-oxo-1-phenyl-1,4-dihydro-quin-oline-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(methanesulfonyl)benzoic acid (50.2 mg, 0.251 mmol), bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (PyBrOP) (140 mg, 0.301 mmol) N,N-diisopropylethylamine (162 mg, 1.25 mmol) and CH2Cl2 (10 mL) was stirred at room temperature for 5 min. After this time, 3-aminomethyl-7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester hydrochloride (intermediate I) (95 mg, 0.251 mmol) was added. The reaction mixture was stirred at room temperature for 3 hr. The reaction mixture was concentrated and purified by preparative reverse-phase HPLC, providing 7-chloro-3-[(4-methanesulfonyl-benzoylamino)-methyl]-4-oxo-1-phenyl-1,4-dihydroquin-oline-2-carboxylic acid methyl ester. MS calcd. for C26H22ClN2O6S [(M+H)+] 525.1, obsd. 525.0.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 3 hr
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-9b48c9ae174547daac1a89cdb1ec01bc
Source dataset
uspto-grants-2013_08
Patent number
US08501732B2

Reaction notes

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