Isonipecotic acid hydrochloride → HCID 86725290, compound

HRID 1403203Notes

Reaction equation

HRID 1403203 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[NH2:6])#[CH:2].[CH:12]1C=CC2N(O)N=NC=2C=1.Cl.[NH:23]1[CH2:31][CH2:30][CH:26]([C:27]([OH:29])=O)[CH2:25][CH2:24]1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]([NH:6][C:27]([CH:26]2[CH2:25][CH2:24][N:23]([CH3:12])[CH2:31][CH2:30]2)=[O:29])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])#[CH:2]

Participants

7

Reactant 5

HCID 22298Isonipecotic acid hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 579250471353245-64-3

Product 1

HCID 86725290HCID 86725290, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Ethynyl-4-methoxyaniline (300 mg, 2 mmol) in DCM (20 mL) was treated in a subsequent manner with HOBt (351 mg, 2.6 mmol), isonipecotic acid hydrochloride (467 mg, 2.6 mmol), DIPEA (906 μL, 5.2 mmol) and finally EDCl (498 mg, 2.6 mmol). The reaction was stirred at room temperature for 1.5 h. The organic phase was washed with saturated sodium hydrogen carbonate solution and dried over sodium sulfate. Evaporation of the solvent left a brownish solid which was employed in the following reaction without further purification.

Workup

  1. washThe organic phase was washed with saturated sodium hydrogen carbonate solution
  2. dry with materialdried over sodium sulfate
  3. customEvaporation of the solvent
  4. waitleft a brownish solid which
  5. customwas employed in the following reaction without further purification

Sources & evidence

ORD record
ord-18ddd676ade54c2f981b5c7c76268d1c
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

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