Triethylamine → HCID 25122028, compound

HRID 37877Notes

Reaction equation

HRID 37877 reaction equation
[CH3:1][C:2]([CH3:18])([CH3:17])[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:26]=[C:27]([C:31]1[N:39]2[C:34]([CH2:35][CH2:36][CH2:37][CH2:38]2)=[CH:33][C:32]=1[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:28](Cl)=[O:29]>C(Cl)Cl>[CH3:1][C:2]([CH3:18])([CH3:17])[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:28](=[O:29])[C:27](=[O:26])[C:31]3[N:39]4[C:34]([CH2:35][CH2:36][CH2:37][CH2:38]4)=[CH:33][C:32]=3[C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 242791974-[4-(2,2-Dimethyl-propyl)-piperazin-1-yl-]-phenylamineHCID 86649692Oxo-(2-phenyl-5,6,7,8-tetrahydro-indolizin-3-yl)-acetyl chloride

Product 1

HCID 25122028HCID 25122028, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To an ice-cold solution of 4-[4-(2,2-dimethyl-propyl)-piperazin-1-yl]-phenylamine (prepared as described in Reference Example 93, 300 mg, 1.21 mmol) and triethylamine (0.33 mL, 2.4 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, 407 mg, 1.41 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-(2,2-dimethyl-propyl)-piperazin-1-yl]-phenyl}-2-oxo-2-(2-phenyl-5,6,7,8-tetrahydro-indolizin-3-yl)-acetamide (220 mg, 36%) 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-27038262d7744d498bc2c42bceb5bb6d
Source dataset
uspto-grants-2013_09
Patent number
US08524705B2

Reaction notes

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