Diisopropylethylamine → 3-chloro-N-ethyl-4-(4-((6-oxo-5,6-dihydropyrido[2,3-e]pyrrolo[1,2-c]pyrimidin-3-yl)methyl)piperazin-1-yl)benzamide

HRID 44320

反応式

HRID 44320 の反応式
O[CH2:2][C:3]1[CH:16]=[N:15][C:6]2[C:7]3[N:8]([CH:12]=[CH:13][CH:14]=3)[C:9](=[O:11])[NH:10][C:5]=2[CH:4]=1.[Cl:17][C:18]1[CH:19]=[C:20]([CH:26]=[CH:27][C:28]=1[N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)[C:21]([NH:23][CH2:24][CH3:25])=[O:22].[I-].C(C[P+](C)(C)C)#N.C(N(C(C)C)C(C)C)C>C(#N)CC>[Cl:17][C:18]1[CH:19]=[C:20]([CH:26]=[CH:27][C:28]=1[N:29]1[CH2:30][CH2:31][N:32]([CH2:2][C:3]2[CH:16]=[N:15][C:6]3[C:7]4[N:8]([CH:12]=[CH:13][CH:14]=4)[C:9](=[O:11])[NH:10][C:5]=3[CH:4]=2)[CH2:33][CH2:34]1)[C:21]([NH:23][CH2:24][CH3:25])=[O:22]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 10514344(Cyanomethyl)trimethylphosphanium iodideHCID 509163263-(hydroxymethyl)pyrido[2,3-e]pyrrolo[1,2-c]pyrimidin-6(5H)-oneHCID 583244573-Chloro-N-ethyl-4-(piperazin-1-yl)benzamide

生成物 1

HCID 509165063-chloro-N-ethyl-4-(4-((6-oxo-5,6-dihydropyrido[2,3-e]pyrrolo[1,2-c]pyrimidin-3-yl)methyl)piperazin-1-yl)benzamide収率 66.5%

試薬・触媒・溶媒 1

HCID 7854Propionitrile溶媒

反応条件

温度
95 °C

実験手順

To a suspension of 3-(hydroxymethyl)pyrido[2,3-e]pyrrolo[1,2-c]pyrimidin-6(5H)-one (25.00 mg, 0.116 mmol), 3-chloro-N-ethyl-4-(piperazin-1-yl)benzamide (38.9 mg, 0.145 mmol) and (cyanomethyl)trimethylphosphonium iodide (45.2 mg, 0.186 mmol) in Propiononitrile (Volume: 1.0 mL) was added N-ethyl-N-isopropylpropan-2-amine (0.101 mL, 0.581 mmol) at 23° C. The reaction was stirred at 95° C. for 6 hr. The suspension was cooled to 23° C., filtered, rinsed with ACN (3×1 mL) and dried in vacuo to provide 3-chloro-N-ethyl-4-(4-((6-oxo-5,6-dihydropyrido[2,3-e]pyrrolo[1,2-c]pyrimidin-3-yl)methyl)piperazin-1-yl)benzamide (0.0359 g, 0.077 mmol, 66.5% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.10 (t, J=7.20 Hz, 3 H) 2.53-2.67 (m, 4 H) 2.98-3.14 (m, 4 H) 3.21-3.30 (m, 2 H) 3.65 (s, 2 H) 6.70-6.77 (m, 1 H) 7.08 (dd, J=3.54, 1.52 Hz, 1 H) 7.19 (d, J=8.59 Hz, 1 H) 7.58 (d, J=1.77 Hz, 1 H) 7.68 (dd, J=3.03, 1.52 Hz, 1 H) 7.77 (dd, J=8.34, 2.02 Hz, 1 H) 7.88 (d, J=2.02 Hz, 1 H) 8.37 (d, J=1.77 Hz, 1 H) 8.44 (t, J=5.43 Hz, 1 H) 11.63 (br. s., 1 H). ESI-MS: m/z 465.4 (M+H)+. mp=266.1-271.2° C.

後処理

  1. temperatureThe suspension was cooled to 23° C.
  2. filtrationfiltered
  3. washrinsed with ACN (3×1 mL)
  4. customdried in vacuo

出典と根拠

ORDレコード
ord-f0d95e12c5984ced85d5ac9db73a6bfa
出典データセット
uspto-grants-2013_09
特許番号
US08541417B2

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