Triethylamine → 1-(3-(5-(4-fluorobenzyl)-3-(pyridin-4-yl)-1H-pyrazol-1-yl)azetidin-1-yl)propan-1-one

HRID 2074099Notes

Reaction equation

HRID 2074099 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][C:7]2[N:11]([CH:12]3[CH2:15][NH:14][CH2:13]3)[N:10]=[C:9]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[CH:8]=2)=[CH:4][CH:3]=1.[C:24](Cl)(=[O:27])[CH2:25][CH3:26].C(N(CC)CC)C>C(Cl)Cl>[F:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][C:7]2[N:11]([CH:12]3[CH2:13][N:14]([C:24](=[O:27])[CH2:25][CH3:26])[CH2:15]3)[N:10]=[C:9]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[CH:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 67092285HCID 67092285, compound

Product 1

HCID 248899891-(3-(5-(4-fluorobenzyl)-3-(pyridin-4-yl)-1H-pyrazol-1-yl)azetidin-1-yl)propan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(5-(4-fluorobenzyl)-1-(azetidin-3-yl)-1H-pyrazol-3-yl)pyridine (75 mg, 0.24 mmol) in CH2Cl2 (2 mL) was added propionyl chloride (22 μL, 0.24 mmol) and triethylamine (37 μL, 0.26 mmol) and the reaction mixture was stirred at room temperature for 2 hours. The solution was then loaded directly onto a pre-wetted Biotage 25M column and purified by flash chromatography (0-5% MeOH/CH2Cl2) to give the title compound as a white solid, 68 mg, 78%. 1H NMR (400 MHz, DMSO-D6) δ ppm 8.57 (d, 2 H), 7.74 (d, 2 H), 7.26 (t, 2 H), 7.16 (t, 2 H), 6.72 (s, 1 H), 5.25-5.34 (m, 1 H), 4.32-4.45 (m, 2 H), 4.07-4.13 (m, 4 H), 2.09 (q, 2 H), 0.97 (t, 3 H); m/z (APCI+) for C21H21N4FO 365.1 (M+H)+.

Workup

  1. custompurified by flash chromatography (0-5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-24cdabd490a0486492d88726268a0f88
Source dataset
uspto-grants-2011_04
Patent number
US07919488B2

Reaction notes

Loading…