1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-(2-(3-(29-Hydroxy-5-oxo-9,12,15,18,21,24,27-heptaoxa-2-thia-6-azanonacosyl)benzamido)-5-(piperidin-1-yl)phenyl)-N-(3-(trifluoromethyl)benzyl)isonicotinamide

HRID 1407995Notes

Reaction equation

HRID 1407995 reaction equation
[F:1][C:2]([F:48])([F:47])[C:3]1[CH:4]=[C:5]([CH:44]=[CH:45][CH:46]=1)[CH2:6][NH:7][C:8]([C:10]1[CH:15]=[CH:14][N:13]=[C:12]([C:16]2[CH:21]=[C:20]([N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:19]=[CH:18][C:17]=2[NH:28][C:29]([C:31]2[CH:32]=[C:33]([CH:41]=[CH:42][CH:43]=2)[CH2:34][S:35][CH2:36][CH2:37][C:38]([OH:40])=O)=[O:30])[CH:11]=1)=[O:9].C(N(C(C)C)CC)(C)C.[NH2:58][CH2:59][CH2:60][O:61][CH2:62][CH2:63][O:64][CH2:65][CH2:66][O:67][CH2:68][CH2:69][O:70][CH2:71][CH2:72][O:73][CH2:74][CH2:75][O:76][CH2:77][CH2:78][O:79][CH2:80][CH2:81][OH:82].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[OH:82][CH2:81][CH2:80][O:79][CH2:78][CH2:77][O:76][CH2:75][CH2:74][O:73][CH2:72][CH2:71][O:70][CH2:69][CH2:68][O:67][CH2:66][CH2:65][O:64][CH2:63][CH2:62][O:61][CH2:60][CH2:59][NH:58][C:38](=[O:40])[CH2:37][CH2:36][S:35][CH2:34][C:33]1[CH:32]=[C:31]([CH:43]=[CH:42][CH:41]=1)[C:29]([NH:28][C:17]1[CH:18]=[CH:19][C:20]([N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:21][C:16]=1[C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][N:13]=1)[C:8]([NH:7][CH2:6][C:5]1[CH:44]=[CH:45][CH:46]=[C:3]([C:2]([F:1])([F:48])[F:47])[CH:4]=1)=[O:9])=[O:30]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 11003164Amino-PEG8-alcoholHCID 566494063-(3-((2-(4-((3-(Trifluoromethyl)benzyl)carbamoyl)pyridin-2-yl)-4-(piperidin-1-yl)phenyl)carbamoyl)benzylthio)propanoic acid

Product 1

HCID 867059322-(2-(3-(29-Hydroxy-5-oxo-9,12,15,18,21,24,27-heptaoxa-2-thia-6-azanonacosyl)benzamido)-5-(piperidin-1-yl)phenyl)-N-(3-(trifluoromethyl)benzyl)isonicotinamideYield 6.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 50 mg of 3-(3-((2-(4-((3-(trifluoromethyl)benzyl)carbamoyl)pyridin-2-yl)-4-(piperidin-1-yl)phenyl)carbamoyl)benzylthio)propanoic acid 1.1, 57 mg of diisopropylethylamine, 27 mg of 23-amino-3,6,9,12,15,18,21-heptaoxatricosan-1-ol, 18 mg of EDCI, and 19 mg of HOBt in 2 mL of DMF was stirred for 24 h. The product was isolated by reverse phase HPLC eluting with 0.05% TFA in a water/acetonitrile gradient to give 5.1 mg of product. MS (ES, m/z): 1028 [M+H]+

Workup

  1. customThe product was isolated by reverse phase HPLC
  2. washeluting with 0.05% TFA in a water/acetonitrile gradient

Sources & evidence

ORD record
ord-3e5940417a1041f2ab08c53993bd2e7a
Source dataset
uspto-grants-2014_12
Patent number
US08916569B2

Reaction notes

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