Diisopropylethylamine → (R)-tert-butyl 2-(N-(4-chlorobenzyl)-4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxamido)ethylcarbamate

HRID 388298

反応式

HRID 388298 の反応式
Cl[C:2]1[C:3]2[C@H:10]([CH3:11])[CH2:9][CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Cl:12][C:13]1[CH:38]=[CH:37][C:16]([CH2:17][N:18]([CH2:27][CH2:28][NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[C:19]([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[O:20])=[CH:15][CH:14]=1.CCN(C(C)C)C(C)C>C(#N)C.O>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:17][N:18]([CH2:27][CH2:28][NH:29][C:30](=[O:36])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35])[C:19]([N:21]2[CH2:22][CH2:23][N:24]([C:2]3[C:3]4[C@H:10]([CH3:11])[CH2:9][CH2:8][C:4]=4[N:5]=[CH:6][N:7]=3)[CH2:25][CH2:26]2)=[O:20])=[CH:37][CH:38]=1

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 59670769(R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidineHCID 67135341tert-butyl 2-(N-(4-chlorobenzyl)piperazine-1-carboxamido)ethylcarbamate

生成物 1

HCID 67134584(R)-tert-butyl 2-(N-(4-chlorobenzyl)-4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxamido)ethylcarbamate収率 30.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

(R)-4-Chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine (46 mg, 0.27 mmol, 1.1 eq.) was added to a solution of the tert-butyl 2-(N-(4-chlorobenzyl)piperazine-1-carboxamido)ethylcarbamate (100 mg, 0.25 mmol) and Hunig's base (0.1 mL, 0.75 mmol, 3 eq.) in acetonitrile (3 mL). The resulting mixture was heated to 80° C. overnight. The reaction mixture was diluted with H2O and extracted with DCM, dried and concentrated to yield (R)-tert-butyl 2-(N-(4-chlorobenzyl)-4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxamido)ethylcarbamate (40 mg, 30%). MS (ESI) m/e (M+H+) 529.

後処理

  1. extractionextracted with DCM
  2. customdried
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-69c5a970ae5c4d0694c51ff4d5dd351e
出典データセット
uspto-grants-2013_02
特許番号
US08377937B2

関連ノート

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