1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 11960469, compound

HRID 1670718Notes

Reaction equation

HRID 1670718 reaction equation
[Br:1][C:2]1[CH:18]=[C:17]([CH:19]2[C:28]3[C:27](=[O:29])[CH2:26][CH:25]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH2:24][C:23]=3[NH:22][C:21]([CH3:36])=[C:20]2[C:37]#[N:38])[CH:16]=[C:15]([O:39][CH3:40])[C:3]=1[O:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9](O)=[O:10].CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.[S:61]1[CH:65]=[CH:64][CH:63]=[C:62]1[CH2:66][NH2:67]>ClCCl>[Br:1][C:2]1[CH:18]=[C:17]([CH:19]2[C:28]3[C:27](=[O:29])[CH2:26][CH:25]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH2:24][C:23]=3[NH:22][C:21]([CH3:36])=[C:20]2[C:37]#[N:38])[CH:16]=[C:15]([O:39][CH3:40])[C:3]=1[O:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([NH:67][CH2:66][C:62]1[S:61][CH:65]=[CH:64][CH:63]=1)=[O:10]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 34005(2-Thienylmethyl)amineHCID 81531DiisopropylethylamineHCID 67023397HCID 67023397, compound

Product 1

HCID 11960469HCID 11960469, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of step b (20 mg) in 2 mL of dichloromethane were added EDCI (7.0 mg), DIPEA (7 μL) and 2-thiophenemethylamine (4.1 μL) and the reaction mixture was stirred for 3 h. at room temperature. The reaction mixture was concentrated and the title compound was obtained after flash column chromatography (silica gel, heptane/ethyl acetate (1/4, v/v), Rf=0.78).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-3eb9e9a06d8544da9f0f288fc7f6f328
Source dataset
uspto-grants-2011_08
Patent number
US07994189B2

Reaction notes

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