Diisopropylethylamine → HCID 178424210, compound

HRID 1695223Notes

Reaction equation

HRID 1695223 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][C:9]([OH:11])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.[CH3:21][C:22]1[C:26]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[CH3:33])=[N:25][NH:24][C:23]=1[NH2:34]>ClCCCl>[CH3:21][C:22]1[C:26]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[CH3:33])=[N:25][NH:24][C:23]=1[NH:34][C:9](=[O:11])[CH2:8][CH2:7][CH2:6][N:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 148556811-Pyrrolidinebutanoic acidHCID 178424209HCID 178424209, compound

Product 1

HCID 178424210HCID 178424210, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a suspension of 4-pyrrolidin-1-yl-butyric acid (118.0 mg, 0.8 mmol, 1.5 eq) in 1,2-dichloroethane (3 mL), N,N′-carbonyldiimidazole (113.0 mg, 0.7 mmol, 1.4 eq) was added and the mixture was stirred at room temperature for 1 hour, then N,N-diisopropyl ethyl amine (87 μL, 0.5 mmol, 1.0 eq) was added and the mixture was stirred at room temperature for further 1 hour until complete dissolution of the suspension. 4-Methyl-5-o-tolyl-2H-pyrazol-3-ylamine (93.5 mg, 0.5 mmol, 1.0 eq) was added and the reaction was stirred for 18 hours, then at 50° C. for 1 day, until the conversion of the less stable ring nitrogen-acylated isomer to the title compound was observed (as monitored by LC-MS). The solvent was removed under reduced pressure, the crude was purified by SiO2 column to give 44.0 mg of the title compound (yield: 27%).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at room temperature for further 1 hour until complete dissolution of the suspension
  3. stirringthe reaction was stirred for 18 hours
  4. waitat 50° C. for 1 day

Sources & evidence

ORD record
ord-cbed115632004c539c8d102b4adc631c
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Reaction notes

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