1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 22184985, compound

HRID 1795232Notes

Reaction equation

HRID 1795232 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12]([CH:14]([NH:19][C:20]([C:22]2[CH:31]=[C:30]([O:32][CH3:33])[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=2)=[O:21])[CH2:15][C:16](O)=[O:17])=[O:13])[CH2:8][CH2:7]1)=[O:5])[CH3:2].Cl.C([O:39][C:40](=[O:43])[CH2:41][NH2:42])(C)(C)C.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>O1CCCC1>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][N:9]([C:12]([CH:14]([NH:19][C:20]([C:22]2[CH:31]=[C:30]([O:32][CH3:33])[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=2)=[O:21])[CH2:15][C:16]([NH:42][CH2:41][C:40]([OH:43])=[O:39])=[O:17])=[O:13])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 10226346HCID 10226346, compound

Product 1

HCID 22184985HCID 22184985, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[1-(4-(ethoxycarbonyl)piperazin-1-yl)carbonyl-2-carboxyethyl]aminocarbonyl-4-methoxyquinoline (50 mg, 0.11 mmol) in tetrahydrofuran (THF) (2 mL) was added glycine t-butyl ester hydrochloride (20 mg, 0.12 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDCI) (23 mg, 0.12 mmol), 1-hydroxybenzotriazole (HOBT) (16 mg, 0.12 mmol) and diisopropylethylamine (DIEA) (0.16 g, 0.12 mmol). The reaction was stirred at ambient temperature overnight. The resultant solution was partitioned between water and ethyl acetate. The organic layer was concentrated in vacuo to afford 2-[1-(4-(ethoxycarbonyl)piperazin-1-yl)carbonyl-2-(((carboxy)methyl)aminocarbonyl)ethyl]aminocarbonyl-4-methoxyquinoline as an oil.

Workup

  1. customThe resultant solution was partitioned between water and ethyl acetate
  2. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-0cc2744f399c4a0284a899a47cf79d20
Source dataset
uspto-grants-2006_04
Patent number
US07026323B2

Reaction notes

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