Ethylamine → HCID 58716665, compound

HRID 2117304Notes

Reaction equation

HRID 2117304 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]([N:23]4[CH2:28][CH2:27][N:26]([CH2:29][C:30]([OH:32])=O)[CH2:25][CH2:24]4)=[O:22])=[CH:17][CH:16]=3)[N:9]=2)=[CH:4][CH:3]=1.C1C=C[C:36]2N(O)N=[N:39][C:37]=2C=1.CCN=C=NCCCN(C)C.C(N)C>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:16]=[CH:17][C:18]([C:21]([N:23]4[CH2:24][CH2:25][N:26]([CH2:29][C:30]([NH:39][CH2:37][CH3:36])=[O:32])[CH2:27][CH2:28]4)=[O:22])=[CH:19][CH:20]=3)[N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6341EthylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 219060052-{4-[(4-{[4-(4-Chlorophenyl)pyrimidin-2-yl]amino}phenyl)carbonyl]piperazinyl}acetic acid

Product 1

HCID 58716665HCID 58716665, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-{4-[(4-{[4-(4-Chlorophenyl)pyrimidin-2-yl]amino}phenyl)carbonyl]piperazinyl}acetic acid (0.200 g, 0.44 mmol) was dissolved in DMF then stirred for 15 minutes in ice-brine solution, then the HOBT (0.072 g, 0.53 mmol] then EDCI (0.102 g, 0.53 mmol) were added and stirred for another 30 minutes. Ethylamine (0.030 mL, 0.53 mmol) was added and the reaction was left to stir at room temp overnight. The reaction was quenched with 10 mL of water and a precipitate formed. The precipitate was colleted by filtration, and purified by preparative HPLC to yield 2-{4-[(4-{[4-(4-chlorophenyl)pyrimidin-2-yl]amino}phenyl)carbonyl]piperazinyl}N-ethylacetamide: HPLC Retention time; 9.508 min. (Method B) M+1; 479.2

Workup

  1. waitthe reaction was left
  2. stirringto stir at room temp overnight
  3. customThe reaction was quenched with 10 mL of water
  4. customa precipitate formed
  5. filtrationThe precipitate was colleted by filtration
  6. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-968ef8c49adc47fca731817c2b7a040e
Source dataset
uspto-grants-2008_10
Patent number
US07442699B2

Reaction notes

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