Diisopropylethylamine → HCID 178479479, compound

HRID 1925209Notes

Reaction equation

HRID 1925209 reaction equation
[NH2:1][C@@H:2]1[CH:7]2[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]2)[CH2:3]1.[ClH:10].N1C=CC([C:16]([NH2:18])=[NH:17])=N1.CCN(C(C)C)C(C)C>CN(C=O)C>[ClH:10].[N:4]12[CH2:9][CH2:8][CH:7]([CH2:6][CH2:5]1)[C@@H:2]([NH:1][C:16]([NH2:18])=[NH:17])[CH2:3]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 719215(3R)-1-Azabicyclo(2.2.2)octan-3-amineHCID 178479321HCID 178479321, compound

Product 1

HCID 178479479HCID 178479479, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of (R)-3-aminoquinuclidine (5.85 g, 46.4 mmol) and pyrazole carbox-amidine hydrochloride (6.80 g, 46.4 mmol) is added Hunig's base (8.07 ml, 46.4 mmol) and DMF (30 ml). The reaction is heated at 70° C. for 40 hours. The reaction is then cooled to room temperature and quenched by adding 400 ml of diethyl ether and stirring at room temperature for 2 hours. Product separates out as a white solid, which is filtered, washed and dried (8.94 g, 94%).

Workup

  1. temperatureThe reaction is then cooled to room temperature
  2. customquenched
  3. additionby adding 400 ml of diethyl ether
  4. filtrationis filtered
  5. washwashed
  6. customdried (8.94 g, 94%)

Sources & evidence

ORD record
ord-865146a99db44bbb99d0205283fc3df0
Source dataset
uspto-grants-2012_05
Patent number
US08178672B2

Reaction notes

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