1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 44218439, compound

HRID 46005Notes

Reaction equation

HRID 46005 reaction equation
[CH:1]1([N:4]([CH2:18][CH2:19][O:20][CH2:21][C:22](O)=[O:23])[S:5]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH3:16])=[CH:10][C:9]=2[CH3:17])(=[O:7])=[O:6])[CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH:55]1([N:58]2[CH2:63][CH2:62][N:61]([C:64]3([CH2:70][N:71]4[CH2:79][C:78]5[C:73](=[CH:74][CH:75]=[CH:76][CH:77]=5)[C:72]4=[O:80])[CH2:69][CH2:68][NH:67][CH2:66][CH2:65]3)[CH2:60][CH2:59]2)[CH2:57][CH2:56]1>ClCCl>[CH:1]1([N:4]([CH2:18][CH2:19][O:20][CH2:21][C:22]([N:67]2[CH2:66][CH2:65][C:64]([N:61]3[CH2:62][CH2:63][N:58]([CH:55]4[CH2:56][CH2:57]4)[CH2:59][CH2:60]3)([CH2:70][N:71]3[CH2:79][C:78]4[C:73](=[CH:74][CH:75]=[CH:76][CH:77]=4)[C:72]3=[O:80])[CH2:69][CH2:68]2)=[O:23])[S:5]([C:8]2[C:9]([CH3:17])=[CH:10][C:11]([O:15][CH3:16])=[CH:12][C:13]=2[CH3:14])(=[O:7])=[O:6])[CH2:2][CH2:3]1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 57436815HCID 57436815, compoundHCID 598201282-(2-(N-Cyclopropyl-4-methoxy-2,6-dimethylphenylsulfonamido)ethoxy)acetic acid

Product 1

HCID 44218439HCID 44218439, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(2-(N-cyclopropyl-4-methoxy-2,6-dimethylphenyl-sulfonamido)ethoxy)acetic acid AC7 (0.306 mmol) in dichloromethane (10 ml/mmol) was added diisopropyl ethylamine (4.0 equiv.) at 0° C. followed by the addition of HOBT (1.0 equiv.) and EDCI (1.5 equiv.). The resultant solution was stirred at 25° C. for 15 min. It was again cooled to 0° C. and a solution of 2-((4-(4-cyclopropylpiperazin-1-yl)piperidin-4-yl)methyl)isoindolin-1-one AM13 (1.2 equiv) in dichloromethane (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: 50%. MS, Rt=3.4 min, m/z=694.5 [MH]+.

Workup

  1. washwashed with saturated ammonium chloride solution, brine, saturated sodium bicarbonate and finally again with brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-e61f95bff930474a974e6fe98f2c67e1
Source dataset
uspto-grants-2013_09
Patent number
US08541573B2

Reaction notes

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