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 970540노트

반응식

HRID 970540 반응식
[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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1567b5f13dea4a488101958bd5648a54
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07312220B2

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