1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 11712792, compound

HRID 1171132Notes

Reaction equation

HRID 1171132 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=3)[C:21](O)=[O:22])[N:16]=2)[NH:11][CH:10]=1.CCN=C=NCCCN(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[CH3:71][N:72]([CH3:81])[CH2:73][CH2:74][N:75]1[CH2:80][CH2:79][NH:78][CH2:77][CH2:76]1>CN(C=O)C>[CH3:71][N:72]([CH3:81])[CH2:73][CH2:74][N:75]1[CH2:80][CH2:79][N:78]([C:21]([C:20]2[CH:24]=[CH:25][CH:26]=[C:18]([C:15]3[N:16]=[C:17]4[C:9]([C:4]5[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=5[O:2][CH3:1])=[CH:10][NH:11][C:12]4=[N:13][CH:14]=3)[CH:19]=2)=[O:22])[CH2:77][CH2:76]1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27362291-(2-(Dimethylamino)ethyl)piperazineHCID 59836116HCID 59836116, compound

Product 1

HCID 11712792HCID 11712792, compoundYield 17.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 3-[7-(2-Methoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-benzoic acid (35 mg, 0.1 mmol), EDCI (77 mg, 0.40 mmol), HBTU (3.8 mg, 0.01 mmol) and diisopropylethylamine (175 μl, 1.0 mmol) in DMF (1 mL) was added 2-(dimethylamino)ethylpiperazine (55 μl, 0.3 mmol). The mixture was stirred at 70° C. for 5 hours before the solvents were removed. The resulting yellow oil was washed with water, dissolved in DMSO and purified on reverse phase HPLC to afford the title compound (8.6 mg, 12% over 2 steps) as yellow solid. MS: m/z 485.2 [MH+].

Workup

  1. customwere removed
  2. washThe resulting yellow oil was washed with water
  3. dissolutiondissolved in DMSO
  4. custompurified on reverse phase HPLC

Sources & evidence

ORD record
ord-b5b3f1d3f8b24660a94e747ea88c7425
Source dataset
uspto-grants-2010_11
Patent number
US07829558B2

Reaction notes

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