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Diisopropylethylamine → (5S)-5-({[6-(4-Chlorophenyl)-3,4-dihydro-2,7-naphthyridin-2(1H)-yl]sulfonyl}methyl)-5-methylimidazolidine-2,4-dione

HRID 643492
Notes
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Reaction equation

HRID 643492 reaction equation
[CH3:1][C@@:2]1([CH2:9][S:10](Cl)(=[O:12])=[O:11])[C:6](=[O:7])[NH:5][C:4](=[O:8])[NH:3]1.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][N:30]=2)[CH2:27][NH:26][CH2:25][CH2:24]3)=[CH:17][CH:16]=1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1.O>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[CH:22]=[C:23]3[C:28](=[CH:29][N:30]=2)[CH2:27][N:26]([S:10]([CH2:9][C@@:2]2([CH3:1])[NH:3][C:4](=[O:8])[NH:5][C:6]2=[O:7])(=[O:12])=[O:11])[CH2:25][CH2:24]3)=[CH:19][CH:20]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 16738713(4S)-(4-methyl-2,5-dioxoimidazolidin-4-yl)methanesulphonyl chlorideHCID 686027826-(4-Chlorophenyl)-1,2,3,4-tetrahydro-2,7-naphthyridine

Product 1

HCID 11561131(5S)-5-({[6-(4-Chlorophenyl)-3,4-dihydro-2,7-naphthyridin-2(1H)-yl]sulfonyl}methyl)-5-methylimidazolidine-2,4-dioneYield 8.5%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

[(4S)-4-Methyl-2,5-dioxoimidazolidin-4-yl]methanesulfonyl chloride (0.086 g, 0.38 mmol) in anhydrous NMP (0.50 mL) was added dropwise to a stirred solution of 6-(4-chlorophenyl)-1,2,3,4-tetrahydro-2,7-naphthyridine (0.046 g, 0.19 mmol), DIPEA (0.066 mL, 0.38 mmol) and anhydrous NMP (1.5 mL) at RT. After the addition was complete the solution was stirred at RT for 1.5 h, then diluted with water (1 mL) and purified by preparative HPLC to afford 0.0070 g (8%) of the title compound as a white solid.

Workup

  1. additionAfter the addition
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-fdfb3c4d00664914971dea9cd641c71f
Source dataset
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07700604B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes