Triethylamine → HCID 67092199, compound

HRID 2074091Notes

Reaction equation

HRID 2074091 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.[CH:38]1([C:41](Cl)=[O:42])[CH2:40][CH2:39]1>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])[C:41]([CH:38]4[CH2:40][CH2:39]4)=[O:42])[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 77637Cyclopropanecarbonyl chlorideHCID 67092328HCID 67092328, compound

Product 1

HCID 67092199HCID 67092199, 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 cyclopropanecarbonyl chloride (34 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, 162 mg, 92%. 1H NMR (rotomers seen, 400 MHz, DMSO-D6) δ ppm 8.43-8.59 (2 H, m), 7.59-7.72 (2 H, m), 7.31 (2 H, dd, J=8.46, 5.68 Hz), 7.15 (2 H, t, J=8.84 Hz), 6.52 (1 H, s), 5.10-5.36 (2 H, m), 4.22-4.60 (2 H, m), 3.95 (3 H, s), 3.03-3.26 (1 H, m), 2.53-3.01 (4 H, m), 1.42-2.10 (5 H, m), 0.62-0.79 (4 H, m); m/z (APCI+) for C27H30N5O2F 476.2 (M+H)+.

Workup

  1. washeluted with 2-8% MeOH/DCM

Sources & evidence

ORD record
ord-20dd3cb3a5814df18bfa58a77b28acc4
Source dataset
uspto-grants-2011_04
Patent number
US07919488B2

Reaction notes

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