Diisopropylethylamine → (R)-4-(2,4-Dimethoxybenzylamino)-3-(4-(8-fluorochroman-4-ylamino)-5-nitropyrimidin-2-ylamino)benzonitrile

HRID 605863노트

반응식

HRID 605863 반응식
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[O:10][CH2:9][CH2:8][C@H:7]2[NH2:12].C(N(CC)C(C)C)(C)C.[CH3:22][O:23][C:24]1[CH:52]=[C:51]([O:53][CH3:54])[CH:50]=[CH:49][C:25]=1[CH2:26][NH:27][C:28]1[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][C:29]=1[NH:36][C:37]1[N:42]=[C:41](SC#N)[C:40]([N+:46]([O-:48])=[O:47])=[CH:39][N:38]=1>CS(C)=O.C1COCC1.CCOC(C)=O>[CH3:22][O:23][C:24]1[CH:52]=[C:51]([O:53][CH3:54])[CH:50]=[CH:49][C:25]=1[CH2:26][NH:27][C:28]1[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][C:29]=1[NH:36][C:37]1[N:42]=[C:41]([NH:12][C@H:7]2[C:6]3[C:11](=[C:2]([F:1])[CH:3]=[CH:4][CH:5]=3)[O:10][CH2:9][CH2:8]2)[C:40]([N+:46]([O-:48])=[O:47])=[CH:39][N:38]=1

참가 물질

7

반응물 3

HCID 81531DiisopropylethylamineHCID 46911919(R)-8-fluorochroman-4-amineHCID 566052112-(5-Cyano-2-{[(2,4-dimethoxyphenyl)methyl]amino}anilino)-5-nitropyrimidin-4-yl thiocyanate

생성물 1

HCID 59704995(R)-4-(2,4-Dimethoxybenzylamino)-3-(4-(8-fluorochroman-4-ylamino)-5-nitropyrimidin-2-ylamino)benzonitrile수율 96.2%

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

(R)-8-Fluorochroman-4-amine (HCl salt, 0.45 g, 2.2 mmol) was dissolved in 1 mL DMSO with 1.7 mL N,N-diisopropylethyl amine (9.7 mmol) in 40 mL anhydrous THF. To this solution was added 0.93 g (2.0 mmol) 4-(2,4-dimethoxybenzylamino)-3-(5-nitro-4-thiocyanatopyrimidin-2-ylamino)benzonitrile. The slightly cloudy mixture was stirred at room temperature for 16 hrs under Argon balloon till HPLC showed the completion of reaction. The mixture became clear then. The reaction mixture was diluted with EtOAc, washed with brine twice, and then dried over Na2SO4. Solvents were removed under vacuum to give 1.1 g dark red solid as the crude product.

후처리

  1. customthe completion of reaction
  2. washwashed with brine twice
  3. dry with materialdried over Na2SO4
  4. customSolvents were removed under vacuum

출처 및 근거

ORD 기록
ord-7ca6aab196f74a56b6331b66d36c3393
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915268B2

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