1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 11563549, compound

HRID 504157Notes

Reaction equation

HRID 504157 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C@H:12]([NH:16][C:17]([C@@H:19]2[CH2:24][CH2:23][CH2:22][CH2:21][N:20]2[S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=2)(=[O:27])=[O:26])=[O:18])[C:13]([OH:15])=O)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.[NH2:48][CH:49]1[CH2:54][CH2:53][O:52][CH2:51][CH2:50]1.CCN=C=NCCCN(C)C>C(Cl)Cl.O>[CH:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][C@H:12]([NH:16][C:17]([C@@H:19]2[CH2:24][CH2:23][CH2:22][CH2:21][N:20]2[S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:35])([F:36])[F:37])[CH:29]=2)(=[O:26])=[O:27])=[O:18])[C:13](=[O:15])[NH:48][CH:49]2[CH2:54][CH2:53][O:52][CH2:51][CH2:50]2)=[CH:9][CH:10]=1)([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 4192234-AminotetrahydropyranHCID 59428652HCID 59428652, compound

Product 1

HCID 11563549HCID 11563549, compoundYield 69.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a room temperature mixture of (S)-3-(4-isopropoxy-phenyl)-2-{[(S)-1-(3-trifluoromethyl-benzenesulfonyl)-piperidine-2-carbonyl]-amino}-propionic acid (96.0 mg, 0.177 mmol) (prepared according to the method described for the preparation of compound 17e, HOBT (29.0 mg, 0.215 mmol), 4-aminotetrahydropyran (19.6 mg, 0.194 mmol), methylene chloride (2 mL), and water (2 mL) was added EDCI (39.0 mg, 0.203 mmol) in one portion. The reaction mixture was stirred at room temperature overnight. The reaction was diluted with methylene chloride, washed with water, dried over MgSO4, filtered, and concentrated. The residue was chromatographed on silica gel eluting with ethyl acetate to afford 77.1 mg (69%) of the title compound as an amorphous white solid. mp: 78.6° C. Rf=0.40 (silica gel, ethyl acetate).

Workup

  1. customprepared
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-a16faa951e9944a28561c8ae1920d3ac
Source dataset
uspto-grants-2010_08
Patent number
US07777042B2

Reaction notes

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