2(1H)-Quinoxalinone, 3,4-dihydro- → tert-butyl N-(3-(1,2,3,4-tetrahydroquinoxalin-3-on-1-carbonyl)benzyl)-N-methylcarbamate

HRID 901963Notes

Reaction equation

HRID 901963 reaction equation
CCN=C=NCCCN(C)C.Cl.[C:13]([C:16]1[CH:17]=[C:18]([CH:29]=[CH:30][CH:31]=1)[CH2:19][N:20]([CH3:28])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])([OH:15])=O.[NH:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[NH:35][CH2:34][C:33]1=[O:42]>CN(C)C1C=CN=CC=1.ClCCl.C(OCC)(=O)C>[N:35]1([C:13]([C:16]2[CH:17]=[C:18]([CH:29]=[CH:30][CH:31]=2)[CH2:19][N:20]([CH3:28])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:15])[C:36]2[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=2)[NH:32][C:33](=[O:42])[CH2:34]1

Participants

7

Reactant 3

HCID 1859492(1H)-Quinoxalinone, 3,4-dihydro-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 224502433-[(Tert-butoxycarbonyl-methyl-amino)-methyl]-benzoic acid

Product 1

HCID 69208344tert-butyl N-(3-(1,2,3,4-tetrahydroquinoxalin-3-on-1-carbonyl)benzyl)-N-methylcarbamateYield 27.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

WSC.HCl (640 mg, 3.4 mmol) and 4-(dimethylamino)pyridine (330 mg, 2.7 mmol) were added to a solution of tert-butyl N-(3-carboxybenzyl)-N-methylcarbamate (700 mg, 2.6 mmol) and 1,2,3,4-tetrahydroquinoxalin-2-one (440 mg, 2.9 mmol) in dichloromethane (20 ml). The mixture was stirred for 18 h, reduced in vacuo and taken up in ethyl acetate. This solution was washed with 0.3N potassium hydrogen sulphate and saturated sodium hydrogen carbonate solutions, dried and reduced. Chromatography (50% EtOAc/50% 60-80 pet.ether) afforded tert-butyl N-(3-(1,2,3,4-tetrahydroquinoxalin-3-on-1-carbonyl) benzyl)-N-methylcarbamate (280 mg, 27%) as an orange oil.

Workup

  1. washThis solution was washed with 0.3N potassium hydrogen sulphate and saturated sodium hydrogen carbonate solutions
  2. customdried

Sources & evidence

ORD record
ord-8d249a5878c04f61aa1bb2d6f190999f
Source dataset
uspto-grants-2008_04
Patent number
US07365065B2

Reaction notes

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