Triethylamine → HCID 67091909, compound

HRID 2074092Notes

Reaction equation

HRID 2074092 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[N:11]([CH2:12][C:13]([N:15]3[CH2:20][CH2:19][CH:18]([NH:21][CH3:22])[CH2:17][CH2:16]3)=[O:14])[N:10]=[C:9]([C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)[CH:8]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[N:11]([CH2:12][C:13]([N:15]3[CH2:16][CH2:17][CH:18]([N:21]([CH3:22])[S:39]([CH3:38])(=[O:41])=[O:40])[CH2:19][CH2:20]3)=[O:14])[N:10]=[C:9]([C:23]3[CH:24]=[CH:25][N:26]=[CH:27][CH:28]=3)[CH:8]=2)=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67092328HCID 67092328, compound

Product 1

HCID 67091909HCID 67091909, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-{[5-(4-fluorobenzyl)-3-pyridin-4-yl-1H-pyrazol-1-yl]acetyl}-N-methylpiperidin-4-amine (150 mg, 0.37 mmol) in DCM (3 mL) at room temperature was added triethylamine (56 μL, 0.40 mmol) followed by methanesulfonyl chloride (29 μL, 0.37 mmol) and the solution stirred for 10 minutes. The solution was then loaded directly onto a pre-wetted Biotage 25M column for flash chromatography and eluted with 2-8% MeOH/DCM to yield the title compound as a white solid, 137 mg, 76%. 1H NMR (400 MHz, DMSO-D6) δ ppm 8.47-8.56 (2 H, m), 7.61-7.68 (2 H, m), 7.23-7.35 (2 H, m), 7.03-7.19 (2 H, m), 6.52 (1 H, s), 5.10-5.29 (2 H, m), 4.37 (1 H, d, J=13.39 Hz), 3.90-3.99 (3 H, m), 3.74-3.89 (1 H, m), 3.06-3.19 (1 H, m), 2.93 (3 H, s), 2.68 (3 H, s), 2.58-2.65 (1 H, m), 1.62-1.77 (3 H, m), 1.42-1.59 (1 H, m); m/z (APCI+) for C24H28N5O3FS 486.2 (M+H)+.

Workup

  1. washeluted with 2-8% MeOH/DCM

Sources & evidence

ORD record
ord-a8f6cbab231344a1be1d4249c26bc817
Source dataset
uspto-grants-2011_04
Patent number
US07919488B2

Reaction notes

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