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

1,8-Diazabicyclo(5.4.0)undec-7-ene → (Tert-butoxy)-n-[4-(2,4-dioxo(1,3-dihydroquinazolin-3-yl))phenyl]carboxamide

HRID 38163
Notes
Print preview

Reaction equation

HRID 38163 reaction equation
[N:1]([C:4]1[CH:13]=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8]C)=O)=[C:2]=[O:3].[C:14]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=1)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].CCN(C(C)C)C(C)C.C1CCN2C(=NCCC2)CC1>C1COCC1>[C:17]([O:16][C:14]([NH:21][C:22]1[CH:23]=[CH:24][C:25]([N:28]2[C:6](=[O:8])[C:5]3[C:4](=[CH:13][CH:12]=[CH:11][CH:10]=3)[NH:1][C:2]2=[O:3])=[CH:26][CH:27]=1)=[O:15])([CH3:20])([CH3:18])[CH3:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81531DiisopropylethylamineHCID 519494Methyl 2-isocyanatobenzoateHCID 688611tert-Butyl (4-aminophenyl)carbamate

Product 1

HCID 91580089(Tert-butoxy)-n-[4-(2,4-dioxo(1,3-dihydroquinazolin-3-yl))phenyl]carboxamideYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-isocyanatobenzoate (0.97 g, 5.5 mmol) and Boc 1,4-phenylenediamine (1.04 g, 5 mmol) in THF (15 mL) was added DIEA (0.87 mL, 5 mmol) and DBU (0.75 mL, 5 mmol). The reaction mixture stirred at room temp for 5 hr, the off-white solid filtered and washed with ethyl ether to give desired compound (1.49 g, 85%). ES-MS (M+Na)+=376.1, (M−tBu+H)+=298.0.

Workup

  1. filtrationthe off-white solid filtered
  2. washwashed with ethyl ether

Sources & evidence

ORD record
ord-f6e11bd17d7c4309932091a3a26a65a6
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08524721B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes