Dicyclohexylcarbodiimide → 4-Chloro-N-[[1-(dimethylamino)cyclopentyl](phenyl)methyl]-2-methylbenzamide

HRID 20849

반응식

HRID 20849 반응식
[NH2:1][CH:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:3]1([N:8]([CH3:10])[CH3:9])[CH2:7][CH2:6][CH2:5][CH2:4]1.CN(C)C1(C(C2C=CC=CC=2)NC(=O)C2C(C)=CC=CC=2C)CCOC1.[Cl:43][C:44]1[CH:52]=[CH:51][C:47]([C:48](O)=[O:49])=[C:46]([CH3:53])[CH:45]=1.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:43][C:44]1[CH:52]=[CH:51][C:47]([C:48]([NH:1][CH:2]([C:3]2([N:8]([CH3:10])[CH3:9])[CH2:7][CH2:6][CH2:5][CH2:4]2)[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:49])=[C:46]([CH3:53])[CH:45]=1

참가 물질

8

반응물 6

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 3482694-Chloro-2-methylbenzoic acidHCID 516892Sodium BicarbonateHCID 11521393{1-[Amino(phenyl)methyl]cyclopentyl}dimethylamineHCID 59347760(+/-)N-[[3-(Dimethylamino)tetrahydro-3-furanyl](phenyl)methyl]-2,6-dimethylbenzamide

생성물 1

HCID 593477824-Chloro-N-[[1-(dimethylamino)cyclopentyl](phenyl)methyl]-2-methylbenzamide수율 43%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of {1-[amino(phenyl)methyl]cyclopentyl}dimethylamine D3 enantiomer 2 (80 mg, 0.37 mmol), 4-chloro-2-methylbenzoic acid (68 mg; 0.40 mmol), HOBt (61 mg; 0.40 mmol) and PS-DCC (310 mg of 1.3 mmol/g loading, 0.40 mmol) in DCM (4 ml) was shaken overnight. Saturated aqueous sodium bicarbonate was added and the mixture separated with a phase-sep cartridge and the organics applied directly to SCX resin. Elution with DCM, methanol and then 1M ammonia in methanol, followed by chromatography eluting with 12-100% ethyl acetate-pentane (SP4 Biotage) afforded the title product (64 mg; 43%). 1H NMR (CDCl3) δ: 0.9-1.0 (1H, m), 1.25-1.40 (1H, m), 1.4-1.6 (2H, m), 1.6-1.75 (2H, m), 1.8-1.9 (2H, m), 2.22 (6H, s), 2.41 (3H, s), 5.09 (1H, d, J=5 Hz), 7.07 (1H, d, J=5 Hz), 7.2-7.4 (8H, m). Mass Spectrum (Electrospray LC/MS): Found 371 (MH+). C22H2735ClN2O requires 370. Ret. time 2.26 min. The title product was converted to the corresponding hydrochloride salt.

후처리

  1. customthe mixture separated with a phase-sep cartridge
  2. washElution with DCM, methanol
  3. washeluting with 12-100% ethyl acetate-pentane (SP4 Biotage)

출처 및 근거

ORD 기록
ord-b47023f147ae4c59b1d092eef245a220
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745642B2

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