2-Dimethylaminopyridine → HCID 86760814, 화합물

HRID 1725756노트

반응식

HRID 1725756 반응식
[CH2:1]=[C:2]1[CH2:6][CH2:5][C:4]([CH:10]([CH3:12])[CH3:11])([C:7]([OH:9])=O)[CH2:3]1.Cl.[F:14][C:15]([F:29])([F:28])[C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1)[CH2:19]N.C[N:31](C1C=CC=CN=1)C.C(N(C(C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC>ClCCl>[F:14][C:15]([F:28])([F:29])[C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([C:24]([F:27])([F:25])[F:26])[CH:23]=1)[CH2:19][CH:3]1[C:2](=[CH2:1])[CH2:6][CH2:5][C:4]1([CH:10]([CH3:12])[CH3:11])[C:7]([NH2:31])=[O:9]

참가 물질

7

반응물 5

HCID 218852-DimethylaminopyridineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 186143561-[3,5-Bis(trifluoromethyl)phenyl]methanamine--hydrogen chloride (1/1)HCID 18614386HCID 18614386, 화합물

생성물 1

HCID 86760814HCID 86760814, 화합물수율 31%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

The solution of 3-methylene-1-isopropylcyclopentanecarboxylic acid from the previous step (1.25 g, 7.44 mmol) 3,5-bis(trifluoromethyl)benzylamine hydrochloride (2.08 g, 7.44 mmol), dimethylaminopyridine (111.0 mg, 0.91 mmol) and diisopropylethylamine (1.29 mL, 7.44 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC, 2.85 g, 14.9 mmol) in dichloromethane (50 mL) was stirred at room temperature for 24 hrs. The reaction mixture was diluted with dichloromethane (100 mL) and washed with water (3×50 mL), brine (1×50 mL), dried (anhydrous sodium sulfate) and the solvent was evaporated under reduced pressure. The crude product was purified via mplc (Lobar Fertigsaule, LiChroprep, 40-63 μm, ethyl acetate/hexanes (1:4)) yielding 910 mg (31%) of pure product. 1H NMR (500 MHz, CDCl3): 7.76 (s, 1H1), 7.70 (s, 2H), 6.20 (bs, 1H), 4.95 (bs, 1H), 4.88 (bs, 1H), 4.65 (dd, J=15.70, 6.40 Hz, 1H), 4.50 (dd, J=15.50, 5.70 Hz, 1H), 2.68 (bd, J=16.20 Hz, 1H), 2.50 to 2.10 (bm, 4H), 1.96 (h, J=6.9 Hz, 1H), 1.74 (m, 1H), 0.87 (d, J=6.9 Hz, 3H), 0.85 (d, J=7.3 Hz, 31).

후처리

  1. washwashed with water (3×50 mL), brine (1×50 mL)
  2. dry with materialdried (anhydrous sodium sulfate)
  3. customthe solvent was evaporated under reduced pressure
  4. customThe crude product was purified via mplc (Lobar Fertigsaule, LiChroprep, 40-63 μm, ethyl acetate/hexanes (1:4))

출처 및 근거

ORD 기록
ord-ce8744b770c043559c03e95e708e2cfe
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07491737B2

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