Triethylamine → HCID 58964295, compound

HRID 1626200Notes

Reaction equation

HRID 1626200 reaction equation
[Br:1][C:2]1[CH:6]=[N:5][N:4]([CH3:7])[C:3]=1[C:8]1[CH:9]=[C:10]([NH2:21])[CH:11]=[CH:12][C:13]=1[O:14][C@@H:15]1[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16]1.[F:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][C:31]=1[F:32])[C:26](Cl)=[O:27].C(N(CC)CC)C>C1COCC1>[Br:1][C:2]1[CH:6]=[N:5][N:4]([CH3:7])[C:3]=1[C:8]1[CH:9]=[C:10]([NH:21][C:26](=[O:27])[C:25]2[CH:29]=[CH:30][C:31]([F:32])=[C:23]([F:22])[CH:24]=2)[CH:11]=[CH:12][C:13]=1[O:14][C@@H:15]1[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27245193,4-Difluorobenzoyl chlorideHCID 58964268HCID 58964268, compound

Product 1

HCID 58964295HCID 58964295, compoundYield 19.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-(4-bromo-2-methyl-2H-pyrazol-3-yl)-4-((R)-1-methyl-pyrrolidin-3-yloxy)-phenylamine (88 mg, 0.25 mmole), 3,4-difluoro-benzoyl chloride (40 μL, 0.30 mmole), and triethylamine (70 μL, 0.5 mmole) in 1 mL THF was stirred at room temperature for 10 minutes. The mixture was purified by HPLC to give the title compound as a white solid (TFA salt, 24 mg, 19% yield). 1H NMR (CD3OD, 400 MHz) δ 2.17-2.31 (m, 1H), 2.71-2.84 (m, 2H), 2.87-2.97 (m, 2H), 3.14-3.25 (m, 1H), 3.38-3.48 (m, 1H), 3.72-3.79 (m, 1H), 3.75 (s, 3H), 3.89-3.97 (m, 1H), 5.17-5.24 (m, 1H), 7.17-7.30 (m, 1H), 7.41-7.47 (m, 1H), 7.56-7.62 (m, 1H), 7.63-7.69 (m, 1H), 7.78-89 (m, 1H), 7.88-7.93 (m, 2H). Exact mass calculated for C22BrH21F2N4O2 490.1, found 491.5, 493.5 (MH+).

Workup

  1. customThe mixture was purified by HPLC

Sources & evidence

ORD record
ord-b71d3d57b06147a09420a1b0c7e7c79c
Source dataset
uspto-grants-2014_07
Patent number
US08785441B2

Reaction notes

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