Diisopropylethylamine → HCID 58324460、化合物

HRID 69684

反応式

HRID 69684 の反応式
O[CH2:2][C:3]1[CH:12]=[N:11][C:10]2[N:9]3[CH2:13][CH2:14][C@H:8]3[C:7](=[O:15])[NH:6][C:5]=2[CH:4]=1.[N:16]1([C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=2)[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.[I-].C(C[P+](C)(C)C)#N.C(N(CC)C(C)C)(C)C>C(#N)CC.CO>[O:15]=[C:7]1[NH:6][C:5]2[CH:4]=[C:3]([CH2:2][N:19]3[CH2:18][CH2:17][N:16]([C:22]4[CH:23]=[CH:24][C:25]([C:26]#[N:27])=[CH:28][CH:29]=4)[CH2:21][CH2:20]3)[CH:12]=[N:11][C:10]=2[N:9]2[CH2:13][CH2:14][C@@H:8]12

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 27339954-(Piperazin-1-yl)benzonitrileHCID 10514344(Cyanomethyl)trimethylphosphanium iodideHCID 58324372HCID 58324372、化合物

生成物 1

HCID 58324460HCID 58324460、化合物収率 6.25%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 7854Propionitrile溶媒

反応条件

温度
90 °C

実験手順

(S)-3-(hydroxymethyl)-7,8-dihydro-5H-azeto[1,2-a]pyrido[3,2-e]pyrazin-6(6aH)-one (103 mg, 0.5 mmol), 4-(piperazin-1-yl)benzonitrile (108 mg, 0.575 mmol), (cyanomethyl)trimethylphosphonium iodide (207 mg, 0.850 mmol) and N,N-diisopropylethylamine (0.437 ml, 2.500 mmol) were suspended in Propiononitrile (Volume: 1.502 ml) and heated in a closed vial at 90° C. for 23 h. The reaction mixture was cooled, diluted with MeOH (2 mL) and purified using preparative HPLC (basic phase). The fractions containing product were concentrated in vacuo and crystallized from water-methanol (3 mL, ˜5:1) The precipitate was filtered and dried in vacuum to afford (S)-4-(4-((6-oxo-6,6a,7,8-tetrahydro-5H-azeto[1,2-a]pyrido[3,2-e]pyrazin-3-yl)methyl)piperazin-1-yl)benzonitrile (11.7 mg, 0.031 mmol, 6.25% yield) as a light brown solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.37-2.47 (m, 4 H) 2.68-2.80 (m, 1 H) 2.94 (tt, J=10.67, 7.26 Hz, 1 H) 3.30 (d, J=4.80 Hz, 4 H) 3.36 (s, 2 H) 3.87-4.00 (m, 1 H) 4.21 (q, J=7.66 Hz, 1 H) 4.93 (t, 1 H) 6.98 (d, J=1.77 Hz, 1 H) 7.00 (d, J=9.09 Hz, 2 H) 7.57 (d, J=9.09 Hz, 2 H) 7.65 (d, J=1.77 Hz, 1 H) 10.34 (s, 1 H). [M+H] calc'd for C21H22N6O, 374; found, 374.

後処理

  1. temperatureThe reaction mixture was cooled
  2. custompurified
  3. additionThe fractions containing product
  4. concentrationwere concentrated in vacuo
  5. customcrystallized from water-methanol (3 mL, ˜5:1) The precipitate
  6. filtrationwas filtered
  7. customdried in vacuum

出典と根拠

ORDレコード
ord-260686477bb645278ea530d32f8d6f78
出典データセット
uspto-grants-2014_09
特許番号
US08822470B2

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