Triethylamine → benzyl 2-((2-amino-3-carbamoylphenyl)carbamoyl)-3,4-dihydroquinoline-1(2H)-carboxylate

HRID 1895549Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH:9]1[C:18]([OH:20])=O)=[O:7])([CH3:4])(C)C.CCN=C=NCCCN(C)C.Cl.[CH:33]1[CH:34]=[CH:35]C2N(O)N=N[C:37]=2[CH:38]=1.C(N(CC)CC)C.[NH2:50][C:51]1[C:59]([NH2:60])=[CH:58][CH:57]=[CH:56][C:52]=1[C:53]([NH2:55])=[O:54]>CN(C=O)C>[NH2:50][C:51]1[C:52]([C:53](=[O:54])[NH2:55])=[CH:56][CH:57]=[CH:58][C:59]=1[NH:60][C:18]([CH:9]1[CH2:10][CH2:11][C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:8]1[C:6]([O:5][CH2:1][C:4]1[CH:35]=[CH:34][CH:33]=[CH:38][CH:37]=1)=[O:7])=[O:20]

Participants

Conditions

Temperature: 55 °C

Procedure

Step-1: To a solution of 1-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid (100 mg, 0.36 mmol) in anhydrous DMF (3 ml) was added EDC.HCl (207 mg, 1.08 mmol), HOBt (73.4 mg, 0.54 mmol) and triethylamine (0.08 ml, 0.54 mmol) at RT and the mixture was stirred for 10 min. To this reaction mixture, 2,3-diaminobenzamide (60 mg, 0.4 mmol) was added and heated to 55° C. over night. The reaction mixture was poured into ice cold water and stirred for 30 min. The precipitate formed was filtered and dried under vacuum to yield benzyl 2-((2-amino-3-carbamoylphenyl)carbamoyl)-3,4-dihydroquinoline-1(2H)-carboxylate. MS (ES+): m/z 2411.30 [M+H]+

Workup

additionThe reaction mixture was poured into ice cold water
stirringstirred for 30 min
customThe precipitate formed
filtrationwas filtered
customdried under vacuum

Sources & evidence

ORD record: ord-adf4f784edd146439a48b92993e8d7c6
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513433B2

Reaction notes

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