Diisopropylethylamine → HCID 56928287, compound

HRID 330844Notes

Reaction equation

HRID 330844 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH3:22])[C:19]([OH:21])=O)=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)[CH3:2].CCN(C(C)C)C(C)C.[NH2:32][C:33]1[N:37]([CH3:38])[N:36]=[C:35]([CH3:39])[CH:34]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C1COCC1>[CH3:38][N:37]1[C:33]([NH:32][C:19](=[O:21])[CH:18]([C:15]2[CH:14]=[CH:13][C:12]([C:11]#[C:10][C:7]3[CH:6]=[CH:5][C:4]([O:3][CH2:1][CH3:2])=[CH:9][CH:8]=3)=[CH:17][CH:16]=2)[CH3:22])=[CH:34][C:35]([CH3:39])=[N:36]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5207211,3-Dimethyl-1H-pyrazol-5-amine2×HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66692139HCID 66692139, compound

Product 1

HCID 56928287HCID 56928287, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 30 mg (0.11 mmol) 2-[4-(4-ethoxy-phenylethynyl)-phenyl]-propionic acid in (XI.2) 3 mL THF are added 55 μL (0.32 mmol) DIPEA, followed by 30 mg (0.11 mmol) chloro-N,N,N,N-tetramethylformamidinium hexafluorophosphate. The mixture is stirred at rt for 30 min. After that time, 12 mg (0.11 mmol) 5-amino-1,3-dimethylpyrazole are added and stirring is continued for 12 h. The solvent is removed and the residue is taken up in 1 mL DMF. 50 μL DIPEA are added, followed by 30 mg TBTU (0.11 mmol) and 12 mg (0.11 mmol) 5-amino-1,3-dimethylpyrazole. Stirring is continued for 12 h. The solvent is removed and the residue is purified by RP-HPLC (narrow gradients, water/ACN+0.1% TFA).

Workup

  1. stirringstirring
  2. waitis continued for 12 h
  3. customThe solvent is removed
  4. addition50 μL DIPEA are added
  5. stirringStirring
  6. waitis continued for 12 h
  7. customThe solvent is removed
  8. customthe residue is purified by RP-HPLC (narrow gradients, water/ACN+0.1% TFA)

Sources & evidence

ORD record
ord-1257c03a5a3748c8bb2b4baa714290e4
Source dataset
uspto-grants-2014_11
Patent number
US08877754B2

Reaction notes

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