1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68777165, compound

HRID 1711133Notes

Reaction equation

HRID 1711133 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][NH:7][CH:8]2[CH2:13][CH2:12][N:11]([CH:14]([CH3:28])[CH2:15][CH2:16][NH:17][C:18]([C:20]3[C:21]([CH3:27])=[N:22][CH:23]=[N:24][C:25]=3[CH3:26])=[O:19])[CH2:10][CH2:9]2)=[CH:2]1.[C:29]([O:33][C:34]([N:36]1[CH2:41][CH2:40][CH:39]([CH2:42][C:43](O)=[O:44])[CH2:38][CH2:37]1)=[O:35])([CH3:32])([CH3:31])[CH3:30].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:29]([O:33][C:34]([N:36]1[CH2:41][CH2:40][CH:39]([CH2:42][C:43](=[O:44])[N:7]([CH:8]2[CH2:9][CH2:10][N:11]([CH:14]([CH3:28])[CH2:15][CH2:16][NH:17][C:18]([C:20]3[C:25]([CH3:26])=[N:24][CH:23]=[N:22][C:21]=3[CH3:27])=[O:19])[CH2:12][CH2:13]2)[CH2:6][C:3]2[CH:4]=[CH:5][S:1][CH:2]=2)[CH2:38][CH2:37]1)=[O:35])([CH3:32])([CH3:31])[CH3:30]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1512539[1-(tert-Butoxycarbonyl)piperidin-4-yl]acetic acidHCID 86629514HCID 86629514, compound

Product 1

HCID 68777165HCID 68777165, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following general procedure E: a solution of 4,6-dimethyl-pyrimidine-5-carboxylic acid (3-{4-[(thiophen-3-ylmethyl)-amino]-piperidin-1-yl}-butyl)-amide (41 mg, 0.1 mmol), 4-carboxymethyl-piperidine-1-carboxylic acid tert-butyl ester (50 mg, 0.22 mmol), EDCI (39 mg, 0.20 mmol), HOBT (27 mg, 0.20 mmol), and DIPEA (0.05 ml, 0.3 mmol) in CH2Cl2 (2 ml) was stirred overnight. Purification of the crude product by column chromatography on silica gel (CH2Cl2/MeOH, 9:1) afforded 4-{[(1-{3-[(4,6-dimethyl-pyrimidine-5-carbonyl)-amino]-1-methyl-propyl}-piperidin-4-yl)-thiophen-3-ylmethyl-carbamoyl]-methyl}-piperidine-1-carboxylic acid tert-butyl ester (50 mg, 80%).

Workup

  1. customPurification of the crude product by column chromatography on silica gel (CH2Cl2/MeOH, 9:1)

Sources & evidence

ORD record
ord-5e52873568ba4e5aafae7be4a8e7ecc3
Source dataset
uspto-grants-2010_09
Patent number
US07790747B2

Reaction notes

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