Triethylamine → HCID 58319377, 화합물

HRID 444699노트

반응식

HRID 444699 반응식
Cl[C:2]([C:11]1[S:12][CH:13]=[C:14]([CH3:17])[C:15]=1[Cl:16])=[C:3]([C:9]#[N:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].Cl.[CH3:19][NH:20][C:21](=[O:25])[C@H:22]([CH3:24])[NH2:23].C(N(CC)CC)C>C(#N)C>[Cl:16][C:15]1[C:14]([CH3:17])=[CH:13][S:12][C:11]=1/[C:2](/[NH:23][C@H:22]([CH3:24])[C:21]([NH:20][CH3:19])=[O:25])=[C:3](\[C:9]#[N:10])/[C:4]([O:6][CH2:7][CH3:8])=[O:5]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 18595779(2S)-2-amino-N-methylpropanamide hydrochlorideHCID 76759590HCID 76759590, 화합물

생성물 1

HCID 58319377HCID 58319377, 화합물수율 60.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of ethyl 3-chloro-3-(3-chloro-4-methyl-2-thienyl)-2-cyanoacrylate (0.351 g, 1.21 mmol, 1 eq.) in 3 ml of acetonitrile was added N-methyl-L-alaninamide hydrochloride (0.201 g, 1.45 mmol, 1.2 eq.) followed by triethylamine (TEA) (0.490 g, 4.84 mmol, 4 eq.). The reaction was microwaved (130° C., 300 s, fixed hold, high absorption) and the solvent evaporated. The residual oil was triturated in ethyl acetate and the white solid removed by filtration. After concentration under vacuum, the residual oil was subjected to column chromatography to give ethyl (2Z)-3-(3-chloro-4-methyl-2-thienyl)-2-cyano-3-{[(2R)-1-(methylamino)-1-oxopropan-2-yl]amino}acrylate (0.26 g, 57% yield) as a mixture of atropoisomers.

후처리

  1. customThe reaction was microwaved
  2. custom(130° C., 300 s, fixed hold, high absorption)
  3. customthe solvent evaporated
  4. customThe residual oil was triturated in ethyl acetate
  5. customthe white solid removed by filtration
  6. concentrationAfter concentration under vacuum

출처 및 근거

ORD 기록
ord-c07b7fe3a21c4708944482a536cc5258
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476197B2

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