Triethylamine → 4-fluoro-3-methyl-N-[3-(2-methyl-2H-pyrazol-3-yl)-4-((S)-1-methyl-pyrrolidin-2-ylmethoxy)-phenyl]-benzamide

HRID 1362970Notes

Reaction equation

HRID 1362970 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([NH2:21])[CH:10]=[CH:11][C:12]=2[O:13][CH2:14][CH:15]2[CH2:19][CH2:18][CH2:17][N:16]2[CH3:20])=[CH:5][CH:4]=[N:3]1.[F:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][C:24]=1[CH3:32].C(N(CC)CC)C>C1COCC1>[F:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([NH:21][C:9]2[CH:10]=[CH:11][C:12]([O:13][CH2:14][C@@H:15]3[CH2:19][CH2:18][CH2:17][N:16]3[CH3:20])=[C:7]([C:6]3[N:2]([CH3:1])[N:3]=[CH:4][CH:5]=3)[CH:8]=2)=[O:28])=[CH:25][C:24]=1[CH3:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27745894-Fluoro-3-methylbenzoyl chlorideHCID 669285023-(2-Methyl-2H-pyrazol-3-yl)-4-(1-methyl-pyrrolidin-2-ylmethoxy)-phenylamine

Product 1

HCID 669281484-fluoro-3-methyl-N-[3-(2-methyl-2H-pyrazol-3-yl)-4-((S)-1-methyl-pyrrolidin-2-ylmethoxy)-phenyl]-benzamideYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-(2-Methyl-2H-pyrazol-3-yl)-4-(1-methyl-pyrrolidin-2-ylmethoxy)-phenylamine (64 mg, 0.23 mmole), 4-fluoro-3-methyl-benzoyl chloride (60 mg, 0.35 mmole), and triethylamine (63.4 μL, 0.46 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, 92 mg, 95% yield). Exact mass calculated for C24H27FN4O2 422.2. found 423.2 (MH+).

Workup

  1. customThe mixture was purified by HPLC

Sources & evidence

ORD record
ord-98ed9f766aba4417bad81bcc870b95b2
Source dataset
uspto-grants-2011_02
Patent number
US07884101B2

Reaction notes

Loading…