2-Dimethylaminopyridine → HCID 86760814、化合物

HRID 1725756ノート

反応式

HRID 1725756 の反応式
[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]

参加物

7

反応物 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、化合物

生成物 1

HCID 86760814HCID 86760814、化合物収率 31%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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))

出典と根拠

ORDレコード
ord-ce8744b770c043559c03e95e708e2cfe
出典データセット
uspto-grants-2009_02
特許番号
US07491737B2

反応ノート

読み込み中…