Diisopropylethylamine → HCID 23550119, compound

HRID 1814703Notes

Reaction equation

HRID 1814703 reaction equation
C(OC(=O)CCNC(=O)C1C=CC(CN)=CC=1)C.C1C2(CCCCC2)CCC(=O)C1.[CH2:31]([O:33][C:34](=[O:59])[CH2:35][CH2:36][NH:37][C:38](=[O:58])[C:39]1[CH:44]=[CH:43][C:42]([CH2:45][NH:46][CH:47]2[CH2:52][CH2:51][C:50]3([CH2:57][CH2:56][CH2:55][CH2:54][CH2:53]3)[CH2:49][CH2:48]2)=[CH:41][CH:40]=1)[CH3:32].C(N(C(C)C)CC)(C)C.[F:69][C:70]1[CH:71]=[C:72]([CH:76]=[C:77]([C:79]([F:82])([F:81])[F:80])[CH:78]=1)[C:73](Cl)=[O:74]>C(#N)C>[CH2:31]([O:33][C:34](=[O:59])[CH2:35][CH2:36][NH:37][C:38](=[O:58])[C:39]1[CH:44]=[CH:43][C:42]([CH2:45][NH:46][CH:47]2[CH2:52][CH2:51][C:50]3([CH2:53][CH2:54][CH2:55][CH2:56][CH2:57]3)[CH2:49][CH2:48]2)=[CH:41][CH:40]=1)[CH3:32].[CH2:31]([O:33][C:34](=[O:59])[CH2:35][CH2:36][NH:37][C:38](=[O:58])[C:39]1[CH:44]=[CH:43][C:42]([CH2:45][N:46]([C:73](=[O:74])[C:72]2[CH:76]=[C:77]([C:79]([F:80])([F:81])[F:82])[CH:78]=[C:70]([F:69])[CH:71]=2)[CH:47]2[CH2:52][CH2:51][C:50]3([CH2:53][CH2:54][CH2:55][CH2:56][CH2:57]3)[CH2:49][CH2:48]2)=[CH:41][CH:40]=1)[CH3:32]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 5193643-Fluoro-5-(trifluoromethyl)benzoyl chlorideHCID 574172Spiro[5.5]undecan-3-oneHCID 22502126HCID 22502126, compoundHCID 23550130HCID 23550130, compound

Product 2

HCID 23550119HCID 23550119, compoundYield 200.2%HCID 23550130HCID 23550130, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

3-[4-(Spiro[5.5]undec-3-ylaminomethyl)benzoylamino]propionic acid ethyl ester was prepared by reductive alkylation of 3-(4-aminomethyl-benzoylamino)propionic acid ethyl ester with spiro[5.5]undecan-3-one. 3-[4-(Spiro[5.5]undec-3-ylaminomethyl)benzoylamino]propionic acid ethyl ester (200 mg, 499 μmol) was dissolved in acetonitrile (5 mL) and diisopropylethylamine (170 μL) and cooled on an ice bath. Commercially available 3-fluoro-5-(trifluoromethyl)benzoylchloride (136 mg, 602 μmol) dissolved in acetonitrile (5 mL) was added dropwise. The reaction was complete within one hour as shown by HPLC. The solvent was evaporated and water (10 mL) was added to the residue followed by saturated sodium bicarbonate (10 mL). The product was extracted using ethyl acetate (2×50 mL). The combined ethyl acetate extracts were washed with water (20 mL) and brine (20 mL). Drying the organic phases over MgSO4 and evaporation of the solvent afforded 3-(4-{[(3-fluoro-5-trifluoromethylbenzoyl)spiro[5.5]undec-3-yl-amino]methyl}benzoylamino)propionic acid ethyl ester (295 mg) which was hydrolyzed using sodium hydroxide to afford the title compound.

Workup

  1. additionwas added dropwise
  2. customThe solvent was evaporated
  3. additionwater (10 mL) was added to the residue
  4. extractionThe product was extracted
  5. washThe combined ethyl acetate extracts were washed with water (20 mL) and brine (20 mL)
  6. customDrying the organic phases
  7. customover MgSO4 and evaporation of the solvent

Sources & evidence

ORD record
ord-351041bc342047979ad8ef5cf357ab37
Source dataset
uspto-grants-2005_04
Patent number
US06875760B2

Reaction notes

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