Diisopropylethylamine → HCID 67457877, compound

HRID 528771Notes

Reaction equation

HRID 528771 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:22][CH2:21][C:12]2=[C:13](Cl)[N:14]3[C:18]([N:19]=[C:11]2[CH2:10][CH2:9]1)=[CH:17][CH:16]=[N:15]3)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:23]1[CH2:26][CH:25]([CH2:27][C:28]([OH:30])=[O:29])[CH2:24]1.CCN(C(C)C)C(C)C>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:22][CH2:21][C:12]2=[C:13]([N:23]3[CH2:26][CH:25]([CH2:27][C:28]([OH:30])=[O:29])[CH2:24]3)[N:14]3[C:18]([N:19]=[C:11]2[CH2:10][CH2:9]1)=[CH:17][CH:16]=[N:15]3)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 117685473-Azetidineacetic acidHCID 4692812210-Chloro-5,6,8,9-tetrahydro-1,4,7,10a-tetraaza-cyclohepta[f]indene-7-carboxylic acid tert-butyl ester

Product 1

HCID 67457877HCID 67457877, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

2.5 g (7.75 mmol) 10-Chloro-5,6,8,9-tetrahydro-1,4,7,10a-tetraaza-cyclohepta[f]indene-7-carboxylic acid tert-butyl ester, 1.1 g (9.1 mmol) azetidin-3-yl-acetic acid and 3 mL (17.4 mmol) DIPEA were suspended in 18 mL ethanol. The reaction mixture was stirred at 75° C. over night. The solvent was evaporated and the residue was taken up in EtOAc and water and was acidified using a KHSO4 solution. The organic layer was dried (Na2SO4) and concentrated. The residue was purified by prep. HPLC to yield the corresponding acid (72% of theory).

Workup

  1. customThe solvent was evaporated
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by prep
  5. customHPLC to yield the corresponding acid (72% of theory)

Sources & evidence

ORD record
ord-082f5df909f9427f851eee7480327657
Source dataset
uspto-grants-2016_05
Patent number
US09346816B2

Reaction notes

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