Diisopropylethylamine → HCID 67457945, compound

HRID 528773Notes

Reaction equation

HRID 528773 reaction equation
Cl[C:2]1[N:3]2[C:7]([N:8]=[C:9]3[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11][C:10]=13)=[CH:6][CH:5]=[N:4]2.[NH:17]1[CH2:20][CH:19]([C:21]([OH:23])=[O:22])[CH2:18]1.CCN(C(C)C)C(C)C>C(O)C>[CH3:16][N:13]1[CH2:12][CH2:11][C:10]2=[C:2]([N:17]3[CH2:20][CH:19]([C:21]([OH:23])=[O:22])[CH2:18]3)[N:3]3[C:7]([N:8]=[C:9]2[CH2:15][CH2:14]1)=[CH:6][CH:5]=[N:4]3

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 931923-azetidinecarboxylic AcidHCID 86667174HCID 86667174, compound

Product 1

HCID 67457945HCID 67457945, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To 1.77 g (7.48 mmol) 10-Chloro-7-methyl-6,7,8,9-tetrahydro-5H-1,4,7,10a-tetraaza-cyclohepta[f]indene in 50 mL ethanol was added 0.83 g (8.22 mmol) 3-azetidinecarboxylic acid and 2.75 mL (15.7 mmol) DIPEA and the reaction mixture was heated at 75° C. for 4 hours. The mixture was concentrated and treated with diethyl ether and methanol. After ultrasound irradiation, a precipitate formed which was collected by filtration. The remaining solution was concentrated and the above mentioned procedure was repeated. The precipitates were combined and dried to yield the desired product as the DIPEA-salt.

Workup

  1. concentrationThe mixture was concentrated
  2. additiontreated with diethyl ether and methanol
  3. customAfter ultrasound irradiation
  4. customa precipitate formed which
  5. filtrationwas collected by filtration
  6. concentrationThe remaining solution was concentrated
  7. customdried

Sources & evidence

ORD record
ord-c3ae89cfbc6e43eb841ab9f444f4ec3e
Source dataset
uspto-grants-2016_05
Patent number
US09346816B2

Reaction notes

Loading…