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

HRID 251043Notes

Reaction equation

HRID 251043 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 (—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-2961c57799ca4db5860393257386823a
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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