Triethylamine → HCID 25095423, compound

HRID 37876Notes

Reaction equation

HRID 37876 reaction equation
[CH3:1][C:2](=[CH2:17])[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1.C(N(CC)CC)C.[O:25]=[C:26]([C:30]1[N:38]2[C:33]([CH2:34][CH2:35][CH2:36][CH2:37]2)=[CH:32][C:31]=1[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:27](Cl)=[O:28]>C(Cl)Cl>[CH3:17][C:2](=[CH2:1])[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:27](=[O:28])[C:26](=[O:25])[C:30]3[N:38]4[C:33]([CH2:34][CH2:35][CH2:36][CH2:37]4)=[CH:32][C:31]=3[C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 668514031-(2-Methyl-allyl)-4-(4-amino-phenyl)-piperazineHCID 86649692Oxo-(2-phenyl-5,6,7,8-tetrahydro-indolizin-3-yl)-acetyl chloride

Product 1

HCID 25095423HCID 25095423, compoundYield 21.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To an ice-cold solution of 4-[4-(2-methyl-allyl)-piperazin-1-yl]-phenylamine (prepared as described in Reference Example 89, 500 mg, 2.16 mmol) and triethylamine (0.6 mL, 4.32 mmol) in dry DCM (12 mL) was added a solution of oxo-(2-phenyl-5,6,7,8-tetrahydro-indolizin-3-yl)-acetyl chloride (prepared as described in Reference Example 21, 726 mg, 2.52 mmol) in DCM (5 mL). The mixture was warmed to room temperature and stirred for 30 min then diluted with DCM, washed successively with water, sodium bicarbonate solution and brine, then dried over sodium sulfate. Concentration gave a residue which was purified by preparative TLC using ethyl acetate and hexane (3:7) as eluent to afford N-{4-[4-(2-methyl-allyl)-piperazin-1-yl]-phenyl}-2-oxo-2-(2-phenyl-5,6,7,8-tetrahydro-indolizin-3-yl)-acetamide (220 mg, 21%) as a yellow powder.

Workup

  1. washwashed successively with water, sodium bicarbonate solution and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationConcentration
  4. customgave a residue which
  5. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-8d62af025a17413e989bdbfd447899f0
Source dataset
uspto-grants-2013_09
Patent number
US08524705B2

Reaction notes

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