Triethylamine → HCID 86672527, compound

HRID 541240Notes

Reaction equation

HRID 541240 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]([N:11]2[CH2:16][CH:15]3[CH:13]([CH:14]3[C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[CH2:12]2)=[O:10])[CH:5]=[CH:6][C:7]=1[CH3:8].CCN(CC)CC.[Cl:32][C:33]1[CH:41]=[CH:40][C:36]([C:37](Cl)=[O:38])=[CH:35][N:34]=1>C(Cl)Cl>[Cl:32][C:33]1[CH:41]=[CH:40][C:36]([C:37]([NH:1][C:2]2[CH:3]=[C:4]([C:9]([N:11]3[CH2:16][CH:15]4[CH:13]([CH:14]4[C:17]4[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=4)[CH2:12]3)=[O:10])[CH:5]=[CH:6][C:7]=2[CH3:8])=[O:38])=[CH:35][N:34]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27821656-Chloronicotinoyl ChlorideHCID 68288889HCID 68288889, compound

Product 1

HCID 86672527HCID 86672527, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-Amino-4-methylphenyl)(6-(4-methoxyphenyl)-3-azabicyclo[3.1.0]hexan-3-yl)methanone (150 mg, 0.47 mmol) and Et3N (0.25 mL, 1.8 mmol) in CH2Cl2 (4 mL) at 0° C. was added 6-chloronicotinoyl chloride (106 mg, 0.6 mmol). The ice bath was removed after the addition. The reaction mixture was stirred at room temperature for 1.5 h and then purified by flash column chromatography with EtOAc in hexane (60%, then 100%) to give the title compound as a white foam (0.172 g, 80% yield). MS [M+H]+: 462, 464.

Workup

  1. customThe ice bath was removed
  2. additionafter the addition
  3. custompurified by flash column chromatography with EtOAc in hexane (60%

Sources & evidence

ORD record
ord-488be44ab6f64a49a21c00642bd19e98
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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