Ammonia → HCID 46195787, compound

HRID 888850Notes

Reaction equation

HRID 888850 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:10]([CH3:12])([CH3:11])[C:9](=[O:13])[N:8]2[CH:14]2[CH:21]3[CH2:22][C:17]4([C:24](O)=[O:25])[CH2:18][CH:19]([CH2:23][CH:15]2[CH2:16]4)[CH2:20]3)=[CH:4][CH:3]=1.O.OC1C2N=N[NH:36]C=2C=CC=1.CCN=C=NCCCN(C)C.Cl.N>ClCCl.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:10]([CH3:12])([CH3:11])[C:9](=[O:13])[N:8]2[CH:14]2[CH:21]3[CH2:22][C:17]4([C:24]([NH2:36])=[O:25])[CH2:18][CH:19]([CH2:23][CH:15]2[CH2:16]4)[CH2:20]3)=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59361438HCID 59361438, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 46195787HCID 46195787, compoundYield 24.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-[2-(4-fluorobenzyl)-3,3-dimethyl-4-oxo-1,2-diazetidin-1-yl]adamantane-1-carboxylic acid (20.0 mg, 0.0520 mmol) prepared in Example 90 in dichloromethane (1 mL) was added with hydroxybenzotriazole monohydrate (12.0 mg, 0.0890 mmol), WSC.HCl (20.0 mg, 0.100 mmol), 30% aqueous solution of ammonia (0.1 mL) at room temperature, and the resultant was stirred at the same temperature for 30 minutes. The reaction solution was added with water and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The obtained residue was purified using Preparative Thin-Layer chromatography (ethyl acetate), and the title compound (5.00 mg, 24.9%) was obtained as a white crystalline powder.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe obtained residue was purified

Sources & evidence

ORD record
ord-c2f4e8a083c547d2914046c9fab60c23
Source dataset
uspto-grants-2012_08
Patent number
US08252781B2

Reaction notes

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