Triethylamine → HCID 67193222, compound

HRID 515331Notes

Reaction equation

HRID 515331 reaction equation
[CH:1]1([CH2:4][NH:5][C:6](=[O:17])[NH:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.[CH3:18][NH:19][CH:20]1[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21]1.C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[CH:1]1([CH2:4][NH:5][C:6](=[O:17])[NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:12]([N:19]([CH:20]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21]3)[CH3:18])=[O:14])=[CH:15][CH:16]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 45089533tert-Butyl 3-(methylamino)pyrrolidine-1-carboxylateHCID 580558194-(3-(Cyclopropylmethyl)ureido)benzoic acid

Product 1

HCID 67193222HCID 67193222, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 4-(3-(cyclopropylmethyl)ureido)benzoic acid (4.99 mmol, 1.170 g), tert-butyl 3-(methylamino)pyrrolidine-1-carboxylate (4.99 mmol, 1 g) and triethylamine (11.98 mmol, 1.670 mL, 1.213 g) in dichloromethane (50 mL) was added N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (5.99 mmol, 1.149 g). The reaction was stirred for 20 hours. Chromatography on silica (eluting with a gradient of dichloromethane to ethyl acetate) gave the intermediate tert-butyl 3-(4-(3-(cyclopropylmethyl)ureido)-N-methylbenzamido)-pyrrolidine-1-carboxylate (2 g).

Workup

  1. washChromatography on silica (eluting with a gradient of dichloromethane to ethyl acetate)

Sources & evidence

ORD record
ord-2aaade43ade64877b337e077a3acaf95
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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