1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 66898741, compound

HRID 18973

Reaction equation

HRID 18973 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][CH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[NH2:41][C:42]1[CH:46]=[CH:45][N:44]([CH2:47][C:48]([CH3:51])([OH:50])[CH3:49])[N:43]=1>ClCCl>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]([C:10](=[O:12])[NH:41][C:42]1[CH:46]=[CH:45][N:44]([CH2:47][C:48]([OH:50])([CH3:49])[CH3:51])[N:43]=1)[CH2:13][CH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 27344062-{[(Tert-butoxy)carbonyl]amino}-3-(oxan-4-yl)propanoic acidHCID 593449381-(3-amino-1H-pyrazol-1-yl)-2-methylpropan-2-ol

Product 1

HCID 66898741HCID 66898741, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 2-t-butoxycarbonylamino-3-(tetrahydro-pyran-4-yl)-propionic acid (500 mg, 1.83 mmol) in dichloromethane (15 mL) was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (285 mg, 1.85 mmol) and 1-hydroxybenzotriazole (260 mg, 1.92 mmol). The reaction mixture was stirred at 25° C. for 2 h followed by the addition of 1-(3-amino-pyrazol-1-yl)-2-methyl-propan-2-ol (prepared in U.S. Pat. Appl. US2008021032 Example 80, 312 mg, 2.01 mmol). The reaction mixture was then stirred for 18 h at 25° C. under nitrogen. The reaction mixture was diluted with dichloromethane, washed with 2N aqueous hydrochloric acid, saturated sodium bicarbonate solution, a saturated sodium chloride solution and dried over magnesium sulfate. The organic layer was concentrated, to afford [1-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-ylcarbamoyl]-2-(tetrahydro-pyran-4-yl)-ethyl]-carbamic acid t-butyl ester (700 mg, 93%) as a white solid: LR-ES-MS m/z calculated for C20H34N4O5 [M]+ 410, observed [M+H]+ 411.

Workup

  1. stirringThe reaction mixture was then stirred for 18 h at 25° C. under nitrogen
  2. washwashed with 2N aqueous hydrochloric acid, saturated sodium bicarbonate solution
  3. dry with materiala saturated sodium chloride solution and dried over magnesium sulfate
  4. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-037bdbfe5e9c46c3b4aa58f137cdee4e
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Linked notes

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