1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-{1'-[(4-methoxyquinolin-2-yl)carbonyl]-4-oxospiro[chroman-2,4'-piperidin]-6-yl}acetamide

HRID 545167

反応式

HRID 545167 の反応式
[CH3:1][CH2:2][N:3]=C=NCCCN(C)C.[OH:12]C(C(F)(F)F)=O.[O:19]=[C:20]1[C:34]2[C:29](=[CH:30][CH:31]=[C:32](CC(N)=O)[CH:33]=2)[O:28][C:22]2([CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH2:21]1.[CH3:39][O:40][C:41]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[N:44]=[C:43]([C:51]([OH:53])=O)[CH:42]=1.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.CCN(CC)CC>[CH3:39][O:40][C:41]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[N:44]=[C:43]([C:51]([N:25]2[CH2:24][CH2:23][C:22]3([CH2:21][C:20](=[O:19])[C:34]4[C:29](=[CH:30][CH:31]=[C:32]([NH:3][C:2](=[O:12])[CH3:1])[CH:33]=4)[O:28]3)[CH2:27][CH2:26]2)=[O:53])[CH:42]=1

参加物

7

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 5945964-Methoxy-2-quinolinecarboxylic acidHCID 866101694-oxospiro[chroman-2,4'-piperidin]-6-ylacetamide TFA salt

生成物 1

HCID 16041575N-{1'-[(4-methoxyquinolin-2-yl)carbonyl]-4-oxospiro[chroman-2,4'-piperidin]-6-yl}acetamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

63.3 g of EDCI was added to a mixture of 16.5 g of 4-oxospiro[chroman-2,4′-piperidin]-6-ylacetamide TFA salt, 61.0 g of 4-methoxyquinoline-2-carboxylic acid, 45.9 g of HOBT, 50 mL of Et3N and 90 mL DMF, at 0° C., and the resulting mixture was stirred at room temperature for 14 hours. The reaction mixture was concentrated under reduced pressure, and the residue was partitioned between ethyl acetate and water. The organic layer was washed with water and aqueous saturated sodium carbonate solution successively, then dried over sodium sulfate, and then concentrated. The residue was purified through silica gel column chromatography (eluted with 3% MeOH/CHCl3), and the intended compound was obtained. 1H-NMR (300 MHz, CDCl3) δ: 8.21 (1H, dd, J=8.5, 1.3 Hz), 7.99 (1H, dd, J=8.5, 1.0 Hz), 7.94 (1H, dd, J=8.9, 2.7 Hz), 7.73 (1H, ddd, J=8.5, 6.9, 1.3 Hz), 7.67 (1H, d, J=2.7 Hz), 7.55 (1H, ddd, J=8.5, 6.9, 1.0 Hz), 7.34 (1H, br.s), 7.09 (1H, s), 7.01 (1H, d, J=8.9 Hz), 4.65-4.55 (1H, m), 4.09 (3H, s), 4.06-3.96 (1H, m), 3.58 (1H, dt, J=2.9, 12.7 Hz), 3.36 (1H, dt, J=2.9, 12.7 Hz), 2.83-2.69 (2H, m), 2.26-2.12 (1H, m), 2.17 (3H, s), 2.10-2.00 (1H, m), 1.96-1.75 (2H, m). MS [M+H]+=460.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water and aqueous saturated sodium carbonate solution successively
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified through silica gel column chromatography (eluted with 3% MeOH/CHCl3)
  7. customthe intended compound was obtained

出典と根拠

ORDレコード
ord-5d49bbfb7f854e2aa5addb337e4cf174
出典データセット
uspto-grants-2011_05
特許番号
US07935712B2

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