1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178476205, compound

HRID 1592472Notes

Reaction equation

HRID 1592472 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:16][C:17]1[C:22]([C:23]([O:26][C:27](=[O:29])[CH3:28])([CH3:25])[CH3:24])=[CH:21][CH:20]=[CH:19][N:18]=1)[CH2:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11]([CH3:15])=[CH:10][N:9]=1.O[C:31]1[N:39]=[CH:38][CH:37]=[CH:36][C:32]=1[C:33](O)=[O:34].CCN=C=NCCCN(C)C.C1C=CC2N([OH:60])N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.CN(C1C=CN=CC=1)C.CO.C(Cl)Cl>[NH4+:1].[OH-:26].[CH3:14][C:13]1[C:8]([CH2:7][N:6]([CH2:16][C:17]2[C:22]([C:23]([O:26][C:27](=[O:29])[CH3:28])([CH3:25])[CH3:24])=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:33]([C:32]2[CH:31]=[N:39][C:38]([OH:60])=[CH:37][CH:36]=2)=[O:34])=[N:9][CH:10]=[C:11]([CH3:15])[CH:12]=1

Participants

11

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 11165441HCID 11165441, compoundHCID 178418543HCID 178418543, compound

Product 2

HCID 14923Ammonium HydroxideHCID 178476205HCID 178476205, compoundYield 38.1%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Using General Procedure G: A solution of acetic acid 1-(2-{[(4-amino-butyl)-(3,5-dimethyl-pyridin-2-ylmethyl)-amino]-methyl}-pyridin-3-yl)-1-methyl-ethyl ester (0.22 g, 0.55 mmol) in DMF (5.5 mL) was treated with 2-hydroxynicotinic acid (100 mg, 0.72 mmol), EDCI (137 mg, 0.72 mmol), HOBT (97 mg, 0.72 mmol), DMAP (13 mg, 0.11 mmol), and DIPEA (0.19 mL, 1.1 mmol) at room temperature for 5 hours. Radial chromatography on a silica gel plate (20:1:1 CH2Cl2:MeOH:NH4OH) afforded acetic acid 1-{2-[((3,5-dimethyl-pyridin-2-ylmethyl)-{4-[(6-hydroxy-pyridine-3-carbonyl)-amino]-butyl}-amino)-methyl]-pyridin-3-yl}-1-methyl-ethyl ester (54.4 mg, 19%).

Sources & evidence

ORD record
ord-613eecfb14f54a80be1ebabaf4a18757
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

Loading…