1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (S)-1-(N-(3,5-Dichlorophenyl)-N-phenylcarbamoyl)-2-(2-(N-methyl-N-(2-methoxybenzyl)amino)ethylaminocarbonyl)-4-(N,N-di-n-pentylcarbamoyl)piperazine

HRID 2226041Notes

Reaction equation

HRID 2226041 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18](=[O:30])[N:19]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:14][C@H:13]2[C:31](O)=[O:32])=[O:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH3:61][O:62][C:63]1[CH:74]=[CH:73][CH:72]=[CH:71][C:64]=1[CH2:65][N:66]([CH3:70])[CH2:67][CH2:68][NH2:69]>>[Cl:8][C:6]1[CH:5]=[C:4]([N:9]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18](=[O:30])[N:19]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:14][C@H:13]2[C:31]([NH:69][CH2:68][CH2:67][N:66]([CH3:70])[CH2:65][C:64]2[CH:71]=[CH:72][CH:73]=[CH:74][C:63]=2[O:62][CH3:61])=[O:32])=[O:11])[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

5

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 6484249N1-(2-methoxybenzyl)-N1-methylethane-1,2-diamineHCID 54538500(S)-1-[N-(3,5-Dichlorophenyl)-N-phenylcarbamoyl]-4-(N,N-di-n-pentylcarbamoyl)piperazine-2-carboxylic acid

Product 1

HCID 54559192(S)-1-(N-(3,5-Dichlorophenyl)-N-phenylcarbamoyl)-2-(2-(N-methyl-N-(2-methoxybenzyl)amino)ethylaminocarbonyl)-4-(N,N-di-n-pentylcarbamoyl)piperazineYield 90%

Procedure

According to the procedure of Example 1, Step E above, 46 mg (0.080 mmole) of (S)-1-[N-(3,5-dichlorophenyl)-N-phenylcarbamoyl]-4-(N,N-di-n-pentylcarbamoyl)piperazine-2-carboxylic acid, 12 mg (0.088 mole) of HOBt, 21 mg (0.112 mmole) of EDAC, and 31 mg (0.16 mmole) of N-(2-methoxybenzyl)-N-methylethylenediamine (from Example 1, Step E b) above) after purification by flash chromatography on 16 g of silica gel eluting with 100:5:CH2Cl2 :methanol: provided 54 mg (90%) of an oil.

Workup

  1. customafter purification by flash chromatography on 16 g of silica gel eluting with 100:5

Sources & evidence

ORD record
ord-2da00f8d6a1a4f28b9f8ba0f24b8a638
Source dataset
uspto-grants-1994_09
Patent number
US05344830

Reaction notes

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