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

HRID 605863ノート

反応式

HRID 605863 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

(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.

後処理

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

出典と根拠

ORDレコード
ord-7ca6aab196f74a56b6331b66d36c3393
出典データセット
uspto-grants-2011_03
特許番号
US07915268B2

反応ノート

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