Triethylamine → HCID 11397050, compound

HRID 751585Notes

Reaction equation

HRID 751585 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:11]3[N:12]([CH:14]=[CH:15][N:16]=3)[CH:13]=2)[CH:5]=[CH:6][CH:7]=1.[C:24]([C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][CH:29]=1)([CH3:27])([CH3:26])[CH3:25].C(N(CC)CC)C>C1(C)C=CC=CC=1.CN(C=O)C>[C:24]([C:28]1[CH:29]=[CH:30][C:31]([C:32]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]3[N:9]=[C:10]([NH:17][C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:11]4[N:12]([CH:14]=[CH:15][N:16]=4)[CH:13]=3)[CH:3]=2)=[O:33])=[CH:35][CH:36]=1)([CH3:27])([CH3:25])[CH3:26]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 743724-tert-Butylbenzoyl chlorideHCID 9835991HCID 9835991, compound

Product 1

HCID 11397050HCID 11397050, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6228DimethylformamideSolvent

Procedure

A solution of [6-(3-amino-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-phenyl-amine (5) (50 mg), 4-tert-butyl-benzoyl chloride (0.83 mL of a 0.2M solution in toluene), and triethylamine (0.034 mL) in toluene (1 mL) and N,N,-dimethylformamide (1 mL) is stirred at room temperature for 16 hr. The mixture is purified by preparative thin layer chromatography over silica gel, eluting with diethyl ether/dichloromethane (1:1) to afford 4-tert-butyl-N-[3-(8-phenylamino-imidazo[1,2-a]pyrazin-6-yl)-phenyl]-benzamide (6) as a cream foam.

Workup

  1. customThe mixture is purified by preparative thin layer chromatography over silica gel
  2. washeluting with diethyl ether/dichloromethane (1:1)

Sources & evidence

ORD record
ord-d0f2a3cd5aad42618d0f2c43563a9a1e
Source dataset
uspto-grants-2008_07
Patent number
US07405295B2

Reaction notes

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