1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-Ethynyl-N-{2-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-benzamide

HRID 1177941

反応式

HRID 1177941 の反応式
CCN(C(C)C)C(C)C.[C:10]([C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=1)#[CH:11].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[NH2:42][CH2:43][C:44]([N:46]1[CH2:51][CH2:50][N:49]([C:52](=[O:64])[C:53]2[CH:58]=[C:57]([F:59])[CH:56]=[CH:55][C:54]=2[C:60]([F:63])([F:62])[F:61])[CH2:48][CH2:47]1)=[O:45]>CN(C=O)C.O>[C:10]([C:12]1[CH:13]=[CH:14][C:15]([C:16]([NH:42][CH2:43][C:44]([N:46]2[CH2:47][CH2:48][N:49]([C:52](=[O:64])[C:53]3[CH:58]=[C:57]([F:59])[CH:56]=[CH:55][C:54]=3[C:60]([F:62])([F:61])[F:63])[CH2:50][CH2:51]2)=[O:45])=[O:18])=[CH:19][CH:20]=1)#[CH:11]

参加物

8

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 5897064-Ethynylbenzoic acidHCID 595595982-Amino-1-[4-(2-trifluoromethyl-5-fluoro-benzoyl)-piperazin-1-yl]-ethanone

生成物 1

HCID 595595974-Ethynyl-N-{2-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-benzamide収率 41.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

DIPEA (263.67 mg, 0.34 mL, 2.04 mmol) was added to a stirred solution of 4-Ethynyl-benzoic acid (100 mg, 0.68 mmol) in DMF (1.5 mL). HOBT (92 mg, 0.68 mmol) and EDCI (156.42 mg, 0.81 mmol) were then added at room temperature. After 2 minutes, 2-amino-1-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone (253 mg, 0.68 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 130 mg (41.1% yield) of 4-Ethynyl-N-{2-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-benzamide. LCMS Purity: 87.29%. 1H NMR (DMSO-d6): δ 8.7 (m, 1H), 8.0-7.8 (m, 3H), 7.6-7.4 (m, 4H), 4.4 (s, 1H), 4.2-4.1 (m, 2H), 3.8-3.4 (m, 3H), 3.2-3.0 (m, 2H).

後処理

  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

出典と根拠

ORDレコード
ord-afd866c37f594f5b806299fae29cb8cd
出典データセット
uspto-grants-2010_11
特許番号
US07842696B2

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