Potassium Carbonate → 1-(2-Dimethylamino-ethyl)-6-methyl-2-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-1,2-dihydro-quinolin-3-carbonitrile

HRID 346641

反応式

HRID 346641 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]([C:13]#[N:14])=[C:5]2[N:15]1[CH2:20][CH2:19][N:18]([C:21]([C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)=[O:22])[CH2:17][CH2:16]1.Cl.[CH:29]([N:32]([CH:36](C)C)[CH2:33]CCl)(C)[CH3:30].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:33][N:32]([CH3:36])[CH2:29][CH2:30][N:8]1[C:9]2[C:4](=[CH:3][C:2]([CH3:1])=[CH:11][CH:10]=2)[C:5]([N:15]2[CH2:16][CH2:17][N:18]([C:21]([C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)=[O:22])[CH2:19][CH2:20]2)=[C:6]([C:13]#[N:14])[C:7]1=[O:12]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 779422-Chloroethyldiisopropylammonium chlorideHCID 210819836-Methyl-2-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-1,2-dihydro-quinolin-3-carbonitrile

生成物 1

HCID 210818711-(2-Dimethylamino-ethyl)-6-methyl-2-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-1,2-dihydro-quinolin-3-carbonitrile収率 34.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of Compound 107 (1 g., 2.64 mmol), 2-(diisopropylamino) ethyl chloride hydrochloride (2.64 g, 13.2 mmol), and potassium carbonate (3.64 g, 26.4 mmol) in DMF was heated overnight at 90° C. The solution was cooled and poured into ice water. The solids formed were filtered, washed by water, and dried. The crude product was purified by flash chromatography eluting with 0–10% methanol in ethylacetate gradient to yield 409 mg (30%) of pale yellow solids. M.P. 110–117° C. 1H NMR (DMSO-d6): δ 0.93 (s, 12H), 2.40 (s, 3H), 2.59 (m, 2H), 3.01 (m, 2H), 3.61 (m, 4H), 3.91 (m, 4H), 4.15 (m, 2H), 7.16 (dd, J=3.4, 4.8 Hz, 1H), 7.49 (m, 2H), 7.58 (m, 1H), 7.69 (s, 1H), 7.80 (d, J=5.2 Hz, 1H). EIMS m/z 506 (M+1). Anal. (C28H35N5O2S) C, H, N.

後処理

  1. temperatureThe solution was cooled
  2. customThe solids formed
  3. filtrationwere filtered
  4. washwashed by water
  5. customdried
  6. customThe crude product was purified by flash chromatography
  7. washeluting with 0–10% methanol in ethylacetate gradient

出典と根拠

ORDレコード
ord-912279033be749e98361f3632411b6ae
出典データセット
uspto-grants-2007_02
特許番号
US07173036B2

関連ノート

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