Triethylamine → HCID 11719495, compound

HRID 1626210Notes

Reaction equation

HRID 1626210 reaction equation
[Cl:1][C:2]1[CH:6]=[N:5][N:4]([CH3:7])[C:3]=1[C:8]1[CH:9]=[C:10]([NH2:22])[CH:11]=[CH:12][C:13]=1[O:14][CH:15]1[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]1.[F:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][C:25]=1[CH3:33].C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:6]=[N:5][N:4]([CH3:7])[C:3]=1[C:8]1[CH:9]=[C:10]([NH:22][C:28](=[O:29])[C:27]2[CH:31]=[CH:32][C:24]([F:23])=[C:25]([CH3:33])[CH:26]=2)[CH:11]=[CH:12][C:13]=1[O:14][CH:15]1[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27745894-Fluoro-3-methylbenzoyl chlorideHCID 58964288HCID 58964288, compound

Product 1

HCID 11719495HCID 11719495, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(4-Chloro-2-methyl-2H-pyrazol-3-yl)-4-(1-methyl-piperidin-4-yloxy)-phenylamine (0.040 g, 0.12 mmol), 4-fluoro-3-methylbenzoyl chloride (0.026 g, 0.12 mmol) and triethylamine (0.016 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 745 as a white solid in 57.0% yield. LCMS m/z (%)=457.4 (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-2e5c93ea842541e5bdd85985e4ecd8ad
Source dataset
uspto-grants-2014_07
Patent number
US08785441B2

Reaction notes

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