Cyclopropanecarboxylic acid → HCID 67500207, compound

HRID 2408194Notes

Reaction equation

HRID 2408194 reaction equation
Cl.[Cl:2][C:3]1[C:7]([NH:8][CH2:9][CH3:10])=[CH:6][N:5]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[N:4]=1.[CH:17]1([C:20]([OH:22])=O)[CH2:19][CH2:18]1.Cl.CN(C)CCCN=C=NCC>ClC(Cl)C>[Cl:2][C:3]1[C:7]([N:8]([CH2:9][CH3:10])[C:20]([CH:17]2[CH2:19][CH2:18]2)=[O:22])=[CH:6][N:5]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[N:4]=1

Participants

5

Reactant 3

HCID 15655Cyclopropanecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67498956HCID 67498956, compound

Product 1

HCID 67500207HCID 67500207, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 3-chloro-N-ethyl-1-(pyridin-3-yl)-1H-pyrazol-4-amine monohydrochloride (0.10 g, 0.0.38 mmol) in dichloroethane (0.75 ml) was added cyclopropanecarboxylic acid (0.03 g, 0.38 mmol) and 4-N,N-dimethylaminopyridine (0.14 g, 1.15 mmol) followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.14 g, 0.77 mmol). The reaction was stirred at room temperature overnight. The reaction mixture was concentrated to dryness and the crude product was purified by reverse phase silica gel chromatography eluting with 0-50% acetonitrile/water to give a white solid (0.03 g, 25%); mp 111-119° C.; 1H NMR (400 MHz, CDCl3) δ 8.96 (d, J=2.5 Hz, 1H), 8.63-8.59 (m, 1H), 8.06 (ddd, J=8.3, 2.6, 1.4 Hz, 1H), 8.01 (s, 1H), 7.46 (dd, J=8.3, 4.7 Hz, 1H), 3.73 (q, J=7.2 Hz, 2H), 1.46 (ddd, J=12.6, 8.1, 4.7 Hz, 1H), 1.16 (t, J=7.2 Hz, 3H), 1.04 (t, J=3.7 Hz, 2H), 0.71 (dd, J=7.7, 3.0 Hz, 2H); ESIMS m/z 291 ([M+H]).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customthe crude product was purified by reverse phase silica gel chromatography
  3. washeluting with 0-50% acetonitrile/water

Sources & evidence

ORD record
ord-fa1a58e505c34406afedffd3ba3ad069
Source dataset
uspto-grants-2014_08
Patent number
US08815271B2

Reaction notes

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