Diethyl Ether → N-(5-Cyclopropyl-1H-pyrazol-3-yl)-N'-[(1S)-1-(4-fluorophenyl)ethyl]pyridine-2,6-diamine

HRID 75878Notes

Reaction equation

HRID 75878 reaction equation
Cl[C:2]1[C:3]([NH:19][C:20]2[CH:24]=[C:23]([CH:25]3[CH2:27][CH2:26]3)[NH:22][N:21]=2)=[N:4][C:5]([NH:9][C@H:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH3:11])=[C:6](Cl)[CH:7]=1.CCOCC>Cl>[CH:25]1([C:23]2[NH:22][N:21]=[C:20]([NH:19][C:3]3[CH:2]=[CH:7][CH:6]=[C:5]([NH:9][C@H:10]([C:12]4[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=4)[CH3:11])[N:4]=3)[CH:24]=2)[CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 69285790HCID 69285790, compound

Product 1

HCID 67427348N-(5-Cyclopropyl-1H-pyrazol-3-yl)-N'-[(1S)-1-(4-fluorophenyl)ethyl]pyridine-2,6-diamineYield 30.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

tert-Butyl 5-cyclopropyl-3-[(6-{[(1S)-1-(4-fluorophenyl)ethyl]amino}pyridin-2-yl-amino]-1H-pyrazole-1-carboxylate (Method 21; 146 mg) was dissolved in a solution of hydrogen chloride in ether (2.0 M, 2 ml, 4 mmol) and the reaction mixture was stirred at room temperature for 4 hours. The solvent was removed and semi-prep HPLC (Gilson) purification gave the title compound (37 mg, 25%). 1H NMR (CDCl3) δ 0.55 (m, 2H), 0.70 (m, 2H), 1.35 (m, 3H), 1.65 (m, 1H), 4.53 (m, 2H), 4.91 (br s, 1H), 6.10 (br s, 1H), 6.70 (m, 1H), 7.00 (m, 2H), 7.25 (m, 3H).

Workup

  1. customThe solvent was removed
  2. customsemi-prep HPLC (Gilson) purification

Sources & evidence

ORD record
ord-e83581802a324505988f3d96a9b30315
Source dataset
uspto-grants-2014_09
Patent number
US08835465B2

Reaction notes

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