Triethylamine → HCID 11510779, compound

HRID 1362978Notes

Reaction equation

HRID 1362978 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][C:12]=1[C:18]1[N:19]([CH3:23])[N:20]=[CH:21][CH:22]=1.[F:24][C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][C:33]=1[F:34])[C:28](Cl)=[O:29].C(N(CC)CC)C>C(Cl)Cl>[F:24][C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][C:33]=1[F:34])[C:28]([NH:17][C:14]1[CH:15]=[CH:16][C:11]([O:10][CH2:9][CH2:8][N:3]2[CH2:4][CH2:5][CH2:6][CH2:7][CH:2]2[CH3:1])=[C:12]([C:18]2[N:19]([CH3:23])[N:20]=[CH:21][CH:22]=2)[CH:13]=1)=[O:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27245193,4-Difluorobenzoyl chlorideHCID 58964262HCID 58964262, compound

Product 1

HCID 11510779HCID 11510779, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-[2-(2-Methyl-piperidin-1-yl)-ethoxy]-3-(2-methyl-2H-pyrazol-3-yl)-phenylamine (0.031 g, 0.1 mmol), 3,4-difluorobenzoyl chloride (0.015 mL, 0.12 mmol) and triethylamine (0.018 mL, 0.13 mmol)) in methylene chloride (1.5 mL) was stirred at room temperature overnight and concentrated to give a crude product that was subjected to a purification by prep HPLC. The corresponding fractions were collected and lyophilized to give a TFA-salt of Compound 459 as a white solid in 88.2% yield. LCMS m/z (%)=455.5 (M+H, 100).

Workup

  1. concentrationconcentrated
  2. customto give a crude product that
  3. customwas subjected to a purification by prep HPLC
  4. customThe corresponding fractions were collected

Sources & evidence

ORD record
ord-d018df50aa3b461499ec63dac16d27b6
Source dataset
uspto-grants-2011_02
Patent number
US07884101B2

Reaction notes

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