Triethylamine → HCID 11662901, compound

HRID 1626216Notes

Reaction equation

HRID 1626216 reaction equation
[F:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][C:12]=2[C:18]2[N:19]([CH3:23])[N:20]=[CH:21][CH:22]=2)[CH2:4][CH2:3]1.[F:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][C:26]=1[Cl:34].C(N(CC)CC)C>C1COCC1>[Cl:34][C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][C:25]=1[F:24])[C:29]([NH:17][C:14]1[CH:15]=[CH:16][C:11]([O:10][CH2:9][CH2:8][N:5]2[CH2:6][CH2:7][CH:2]([F:1])[CH2:3][CH2:4]2)=[C:12]([C:18]2[N:19]([CH3:23])[N:20]=[CH:21][CH:22]=2)[CH:13]=1)=[O:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27365483-Chloro-4-fluorobenzoyl ChlorideHCID 58964271HCID 58964271, compound

Product 1

HCID 11662901HCID 11662901, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-[2-(4-fluoro-piperidin-1-yl)-ethoxy]-3-(2-methyl-2H-pyrazol-3-yl)-phenylamine (80 mg, 0.25 mmol), 4-fluoro-3-chlorobenzoyl chloride (48 mg, 0.25 mmol), and triethylamine (0.3 mL) in THF (3 mL) was stirred at r.t. for 10 min. The solvent was concentrated in vacuo and the crude was purified by HPLC to give the title compound (58 mg, 50%) as a white solid as TFA salt. 1H NMR (acetone-d6, 400 MHz) δ 2.02-2.24 (m, 4H), 3.08-3.18 (m, 2H), 3.32-3.42 (m, 2H), 3.63 (t, J=4.55 Hz, 2H), 3.80 (s, 3H), 4.59 (t, J=4.55 Hz, 2H), 4.91-5.03 (m, 1H), 6.30 (d, J=1.77 Hz, 1H), 7.23 (d, J=8.84 Hz, 1H), 7.43-7.51 (m, 2H), 7.81 (t, J=2.27 Hz, 1H), 7.91-7.97 (m, 1H), 8.02-8.08 (m, 1H), 8.18 (dd, J=2.53, 7.33 Hz, 1H), 9.71 (s, 1H). Exact mass calculated for C24H25ClF2N4O2 503.1, found 504.1/506.1 (MH+).

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. customthe crude was purified by HPLC

Sources & evidence

ORD record
ord-42f16a539be34632983c09aff345bbf6
Source dataset
uspto-grants-2014_07
Patent number
US08785441B2

Reaction notes

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