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

Triethylamine → (4-Isopropyl-piperazin-1-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone

HRID 1798547
Notes
Print preview

Reaction equation

HRID 1798547 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([B:10]([OH:12])[OH:11])=[CH:6][CH:5]=1)([OH:3])=O.CN(C(ON1N=N[C:23]2[CH:24]=CC=N[C:22]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N([CH2:42][CH3:43])CC)C.[CH:44]([N:47]1[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1)([CH3:46])[CH3:45].[CH3:53]COC(C)=O>>[CH:44]([N:47]1[CH2:52][CH2:51][N:50]([C:1]([C:4]2[CH:9]=[CH:8][C:7]([B:10]3[O:12][C:23]([CH3:24])([CH3:22])[C:42]([CH3:43])([CH3:53])[O:11]3)=[CH:6][CH:5]=2)=[O:3])[CH2:49][CH2:48]1)([CH3:46])[CH3:45]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 780131-IsopropylpiperazineHCID 3121834-Carboxyphenylboronic AcidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 68756040
(4-Isopropyl-piperazin-1-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone

Procedure

4-Carboxyphenylboronic acid, pinacol ester (1.0 eq, 2.01 mmol, 500 mg) and HATU (2.0 eq, 4.02 mmol, 1.53 g) are mixed together in DMF peptide grade (10 mL). Triethylamine (1.2 eq, 2.41 mmol, 0.34 mL) is then added dropwise and the resulting reaction solution is allowed to stir at room temperature for 15 minutes. Isopropylpiperazine (1.2 eq, 2.41 mmol, 0.35 mL) is then added dropwise and the reaction mixture is stirred at room temperature overnight. The reaction mixture is dissolved in EtOAc and washed with water. The organic layer is dried over drying agent MgSO4, filtered and the organic solvent is reduced in vacuo and dried under vacuum at 40° C. to afford the title compound; [M+H]+=359.

Workup

  1. customthe resulting reaction solution
  2. stirringthe reaction mixture is stirred at room temperature overnight
  3. washwashed with water
  4. customThe organic layer is dried
  5. dry with materialover drying agent MgSO4
  6. filtrationfiltered
  7. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-8ecc25e677084acdbd058531bd897948
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08343966B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes