Cyclopentylamine → HCID 59559648, compound

HRID 1177937Notes

Reaction equation

HRID 1177937 reaction equation
CCN(C(C)C)C(C)C.[O:10]=[C:11]([N:25]1[CH2:30][CH2:29][N:28]([C:31](=[O:42])[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[C:38]([F:41])([F:40])[F:39])[CH2:27][CH2:26]1)[CH2:12][NH:13][C:14](=[O:24])[C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=1.C1[CH:44]=[CH:45][C:46]2[N:51](O)N=N[C:47]=2[CH:48]=1.CCN=C=NCCCN(C)C.C1(N)CCCC1>CN(C=O)C.O>[CH:46]1([NH:51][C:19](=[O:21])[C:18]2[CH:22]=[CH:23][C:15]([C:14]([NH:13][CH2:12][C:11](=[O:10])[N:25]3[CH2:26][CH2:27][N:28]([C:31](=[O:42])[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=4[C:38]([F:41])([F:40])[F:39])[CH2:29][CH2:30]3)=[O:24])=[CH:16][CH:17]=2)[CH2:45][CH2:44][CH2:48][CH2:47]1

Participants

8

Reactant 5

HCID 2906CyclopentylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 25164927HCID 25164927, compound

Product 1

HCID 59559648HCID 59559648, compoundYield 34.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (83.75 mg, 0.1 mL, 0.64 mmol) was added to a stirred solution of N-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-terephthalamic acid (100 mg, 0.21 mmol) in DMF (1 mL). HOBT (29.26 mg, 0.21 mmol) and EDCI (41.4 mg, 0.21 mmol) were then added at room temperature. After 2 minutes, cyclopentylamine (18.39 mg, 0.21 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and the product was extracted with EtOAc and the organic layer was washed with 5% sodium bicarbonate solution followed by brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to get the residue. The obtained residue was recrystallized from a mixture of EtOAc and ether to afford 38 mg (33% yield) of N-cyclopentyl-N′-{2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-terephthalamide. LCMS Purity: 91.36%. 1H NMR (CDO3): δ 7.8-7.7 (m, 7H), 7.7-7.5 (m, 2H), 7.4-7.2 (m, 2H), 6.1 (d, 1H), 4.5-4.4 (q, 1H), 4.4-4.2 (m, 2H), 4.1-3.8 (m, 2H), 3.8-3.4 (m, 5H), 3.2 (m, 2H), 2.1 (m, 2H), 1.7 (m, 3H), 1.5 (m, 2H).

Workup

  1. extractionthe product was extracted with EtOAc
  2. washthe organic layer was washed with 5% sodium bicarbonate solution
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto get the residue
  6. customThe obtained residue was recrystallized from a mixture of EtOAc and ether

Sources & evidence

ORD record
ord-9c7e0d8e30d440f586f50b45c07839cc
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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