Thionyl Chloride → Ethyl trans(+/-)-2-[(2-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-2,3-dihydro-1H-inden-5-yl)carbamoyl]cyclopropanecarboxylate

HRID 1425057Notes

Reaction equation

HRID 1425057 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:9]([OH:11])=O)[NH:5][C:6]=1[CH2:7][CH3:8].S(Cl)(Cl)=O.[NH2:16][CH:17]1[CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([NH:26][C:27]([C@@H:29]3[CH2:31][C@H:30]3[C:32]([O:34][CH2:35][CH3:36])=[O:33])=[O:28])[CH:23]=2)[CH2:18]1>N1C=CC=CC=1>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([NH:16][CH:17]2[CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([NH:26][C:27]([C@@H:29]4[CH2:31][C@H:30]4[C:32]([O:34][CH2:35][CH3:36])=[O:33])=[O:28])[CH:23]=3)[CH2:18]2)=[O:11])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 675489294-chloro-5-ethyl-1H-imidazole-2-carboxylic acidHCID 68416342Ethyl trans(+/-)-2-[(2-amino-2,3-dihydro-1H-inden-5-yl)carbamoyl]cyclopropanecarboxylate

Product 1

HCID 68414544Ethyl trans(+/-)-2-[(2-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-2,3-dihydro-1H-inden-5-yl)carbamoyl]cyclopropanecarboxylateYield 93.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The same operation as in Example (91c) was performed using 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid (0.23 g, 1.32 mmol), thionyl chloride (4 mL), ethyl trans(±)-2-[(2-amino-2,3-dihydro-1H-inden-5-yl)carbamoyl]cyclopropanecarboxylate obtained in Example (98a) (95 mg, 0.24 mmol) and pyridine (5 mL). Purification by silica gel column chromatography (elution solvent: hexane/ethyl acetate=1/2, 3/2, 1/0) gave 0.10 g of the title compound as a light yellow solid (92%).

Workup

  1. customPurification
  2. washby silica gel column chromatography (elution solvent: hexane/ethyl acetate=1/2, 3/2, 1/0)

Sources & evidence

ORD record
ord-eccb5f36d0404777aacaa6fa4fa68e94
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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