Triethylamine → HCID 59698847, compound

HRID 2237558Notes

Reaction equation

HRID 2237558 reaction equation
Br[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11](=[O:28])[CH2:12][C:13]2[N:14]=[C:15]([NH:18][C:19](=[O:27])[C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[S:16][CH:17]=2)[CH2:7][CH2:6]1)=[O:4].[NH2:29][CH2:30][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.C(N(CC)CC)C>C1COCC1>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([C:19]([NH:18][C:15]2[S:16][CH:17]=[C:13]([CH2:12][C:11]([N:8]3[CH2:9][CH2:10][N:5]([C:3](=[O:4])[CH2:2][NH:29][CH2:30][CH:31]4[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]4)[CH2:6][CH2:7]3)=[O:28])[N:14]=2)=[O:27])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76688CyclohexanemethylamineHCID 59698867HCID 59698867, compound

Product 1

HCID 59698847HCID 59698847, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

55.2 To a stirred mixture of 100 mg N-(4-{2-[4-(2-bromo-acetyl)-piperazin-1-yl]-2-oxo-ethyl}-thiazol-2-yl)-4-chloro-benzamide in 5 ml THF at r.t. were added 0.04 ml (aminomethyl)cyclohexane and 0.09 ml triethylamine. After 48 hrs stirring at r.t. under argon atmosphere, the reaction mixture was concentrated. The crude product was purified by chromatography on silica using a gradient from CH2Cl2 to CH2Cl2/MeOH 95:5 in 20 min to give 19 mg 4-chloro-N-[4-(2-{4-[2-(cyclohexylmethyl-amino)-acetyl]-piperazin-1-yl}-2-oxo-ethyl)-thiazol-2-yl]-benzamide. White solid. MS 518.5 ([M+H]+)

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customThe crude product was purified by chromatography on silica using a gradient from CH2Cl2 to CH2Cl2/MeOH 95:5 in 20 min

Sources & evidence

ORD record
ord-6671de52fedc406fb47544da702f97ae
Source dataset
uspto-grants-2010_05
Patent number
US07718659B2

Reaction notes

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