1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → Ethyl trans(+/-)-2-[(2-amino-2,3-dihydro-1H-inden-5-yl)carbamoyl]cyclopropanecarboxylate

HRID 43580Notes

Reaction equation

HRID 43580 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6](C(OC(C)(C)C)=O)[CH2:5]2.[CH2:18]([O:20][C:21]([C@@H:23]1[CH2:25][C@H:24]1[C:26]([OH:28])=O)=[O:22])[CH3:19].CC[N:31]=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.ClCCl>[NH2:31][CH:6]1[CH2:5][C:4]2[C:8](=[CH:9][CH:10]=[C:2]([NH:1][C:26]([C@@H:24]3[CH2:25][C@H:23]3[C:21]([O:20][CH2:18][CH3:19])=[O:22])=[O:28])[CH:3]=2)[CH2:7]1

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11535603(1R,2R)-2-(ethoxycarbonyl)cyclopropane-1-carboxylic acidHCID 86712355tert-butyl 5-amino-1,3-dihydro-2H-inden-2-carboxylate

Product 1

HCID 68416342Ethyl trans(+/-)-2-[(2-amino-2,3-dihydro-1H-inden-5-yl)carbamoyl]cyclopropanecarboxylateYield 81%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The same operation as in Example (93a) was performed using tert-butyl 5-amino-1,3-dihydro-2H-inden-2-carboxylate (described in Andronati, S. A.; Krys'ko, A. A.; Chugunov, B. M.; Kabanova, T. A.; Artemenko, A. G.; Russ. J. Org. Chem.; 42; 8; 2006; 1174-1182, 0.19 g, 0.77 mmol), trans-2-(ethoxycarbonyl)cyclopropanecarboxylic acid (described in Wessjohann, Ludger A.; Fulhorst, Michael; Zakharova, Svetlana; Pol. J. Chem.; 80; 4; 2006; 673-678, 182 mg, 1.15 mmol), WSC hydrochloride (0.29 g, 1.5 mmol), DMAP (10 mg) and dichloromethane (20 mL). Purification by silica gel column chromatography (elution solvent: hexane/ethyl acetate=4/1, 2/1, 1/1, 1/2) gave 0.24 g of the title compound as a colorless solid (81%).

Workup

  1. customPurification
  2. washby silica gel column chromatography (elution solvent: hexane/ethyl acetate=4/1, 2/1, 1/1, 1/2)

Sources & evidence

ORD record
ord-0c8617ff5e2f460ca1b65b0dd92cc169
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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