HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 1895549
Notes
Print preview

Reaction equation

HRID 1895549 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 104870292,3-DiaminobenzamideHCID 198232051-((Tert-butoxy)carbonyl)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid

Product 1

HCID 66889373
benzyl 2-((2-amino-3-carbamoylphenyl)carbamoyl)-3,4-dihydroquinoline-1(2H)-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. additionThe reaction mixture was poured into ice cold water
  2. stirringstirred for 30 min
  3. customThe precipitate formed
  4. filtrationwas filtered
  5. 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

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes