1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 44218283, compound

HRID 46006Notes

Reaction equation

HRID 46006 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[S:9]([N:12]([CH2:16][CH2:17][O:18][CH2:19][C:20](O)=[O:21])[CH:13]1[CH2:15][CH2:14]1)(=[O:11])=[O:10].C(N(C(C)C)CC)(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.[CH:55]1([N:58]2[CH2:63][CH2:62][N:61]([C:64]3([CH2:70][NH:71][C:72](=[O:79])[C:73]4[CH:78]=[CH:77][N:76]=[CH:75][CH:74]=4)[CH2:69][CH2:68][NH:67][CH2:66][CH2:65]3)[CH2:60][CH2:59]2)[CH2:57][CH2:56]1>ClCCl.CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[S:9]([N:12]([CH2:16][CH2:17][O:18][CH2:19][C:20]([N:67]1[CH2:66][CH2:65][C:64]([CH2:70][NH:71][C:72](=[O:79])[C:73]2[CH:78]=[CH:77][N:76]=[CH:75][CH:74]=2)([N:61]2[CH2:60][CH2:59][N:58]([CH:55]3[CH2:56][CH2:57]3)[CH2:63][CH2:62]2)[CH2:69][CH2:68]1)=[O:21])[CH:13]1[CH2:14][CH2:15]1)(=[O:10])=[O:11]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 57453429HCID 57453429, compoundHCID 57916235HCID 57916235, compound

Product 1

HCID 44218283HCID 44218283, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of 2-(2-(2-chloro-N-cyclopropyl-6-methylphenylsulfonamido)-ethoxy)acetic acid AC8 (0.225 mmol) in dichloromethane (10 ml/mmol) was added diisopropyl ethylamine (4 equiv.) at 0° C. followed by the addition of HOBT (1.0 equiv.) and EDCI (1.5 equiv.). The resulting solution was stirred at 25° C. for 15 min. It was again cooled to 0° C. and a solution of N-((4-(4-cyclopropyl-piperazin-1-yl)piperidin-4-yl)methyl)isonicotinamide dihydrochloride AM12 (1.2 equiv.) in DMF (2 ml) was added. The reaction mixture was stirred for 16 h at 25° C. The mixture was diluted with dichloromethane, washed with saturated ammonium chloride solution, brine, saturated sodium bicarbonate and finally again with brine. The organic layer was dried over sodium sulfate and evaporated to dryness under reduced pressure to give the crude product which was purified by column chromatography. Yield: 55%. MS, Rt=2.8 min, m/z=673.4 [MH]+.

Workup

  1. temperatureIt was again cooled to 0° C.
  2. stirringThe reaction mixture was stirred for 16 h at 25° C
  3. washwashed with saturated ammonium chloride solution, brine, saturated sodium bicarbonate and finally again with brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-13b1eab9be1543a69f52f40536d97ad1
Source dataset
uspto-grants-2013_09
Patent number
US08541573B2

Reaction notes

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