1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86605543, compound

HRID 2117939Notes

Reaction equation

HRID 2117939 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([CH2:26][C:27]2[CH:35]=[CH:34][C:30]([C:31]([OH:33])=O)=[CH:29][CH:28]=2)=[C:8]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:14][CH:13]=2)[N:9]=1)(=[O:3])[CH3:2].Cl.CN.ON1C2C=CC=CC=2N=N1.[CH2:49]([N:51]=[C:52]=NCCCN(C)C)C>ClCCl.C(Cl)(Cl)Cl>[C:1]([NH:4][C:5]1[S:6][C:7]([CH2:26][C:27]2[CH:28]=[CH:29][C:30]([C:31]([N:51]([CH3:52])[CH3:49])=[O:33])=[CH:34][CH:35]=2)=[C:8]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:20])[O:21][C:22]([CH3:24])([CH3:25])[CH3:23])=[CH:14][CH:13]=2)[N:9]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 6364545Methylamine hydrochlorideHCID 21914811HCID 21914811, compound

Product 1

HCID 86605543HCID 86605543, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-{[2-(acetylamino)-4-(2-{4-[(tert-butoxycarbonyl)amino]phenyl}ethyl)-1,3-thiazol-5-yl]methyl}benzoic acid (50 mg) in 0.5 ml of dichloromethane were added methylamine hydrochloride (10.7 mg), 1-hydroxybenzotriazole (20.4 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (55.3 μl), then, the mixture was stirred for 3. hrs. at 25° C. The reaction mixture was diluted with 10 ml of chloroform and washed with water and brine. The organic layer was dried over magnesium sulfate and evaporated under vaccum. The residue was triturated with ethyl acetate and diisopropylether, and collected by filtration to give tert-butyl {4-[2-(2-(acetylamino)-5-{4-[(dimethylamino)carbonyl]benzyl}-1,3-thiazol-4-yl)ethyl]phenyl}carbamate as a pale yellow solid.

Workup

  1. customat 25° C
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated under vaccum
  5. customThe residue was triturated with ethyl acetate and diisopropylether
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-7bb0c06b951141adab4376aa0b4d22f5
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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