1-Phenylpiperazine → N-{[4-({(1R)-3-(dimethylamino)-1-[(phenylthio)methyl]propyl}amino)-3-nitrophenyl]sulfonyl}-4-phenylpiperazine-1-carboxamide

HRID 900069ノート

反応式

HRID 900069 の反応式
[C:1]1([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.ClC(Cl)(O[C:24](=[O:30])OC(Cl)(Cl)Cl)Cl.[CH3:32][N:33]([CH3:59])[CH2:34][CH2:35][C@@H:36]([NH:45][C:46]1[CH:51]=[CH:50][C:49]([S:52]([NH2:55])(=[O:54])=[O:53])=[CH:48][C:47]=1[N+:56]([O-:58])=[O:57])[CH2:37][S:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>ClCCl.CN(C1C=CN=CC=1)C>[CH3:59][N:33]([CH3:32])[CH2:34][CH2:35][C@@H:36]([NH:45][C:46]1[CH:51]=[CH:50][C:49]([S:52]([NH:55][C:24]([N:10]2[CH2:11][CH2:12][N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:8][CH2:9]2)=[O:30])(=[O:53])=[O:54])=[CH:48][C:47]=1[N+:56]([O-:58])=[O:57])[CH2:37][S:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

参加物

7

反応物 4

HCID 70961-PhenylpiperazineHCID 8471TriethylamineHCID 94429TriphosgeneHCID 11502754(R)-4-((4-(Dimethylamino)-1-(phenylthio)butan-2-yl)amino)-3-nitrobenzenesulfonamide

生成物 1

HCID 10196923N-{[4-({(1R)-3-(dimethylamino)-1-[(phenylthio)methyl]propyl}amino)-3-nitrophenyl]sulfonyl}-4-phenylpiperazine-1-carboxamide収率 41%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

A solution of N-phenylpiperazine (30 mg, 0.185 mmol) in dichloromethane (2 mL) was treated with triethylamine (77 μL, 0.555 mmol), cooled to 0° C., treated with triphosgene (33 mg, 0.111 mmol), warmed to room temperature, stirred for 1 hour, treated with 4-({(1R)-3-(dimethylamino)-1-[(phenylthio)methyl]propyl}amino)-3-nitrobenzenesulfonamide (prepared according to the procedure described in commonly owned U.S. patent application Ser. No. 09/957,256, filed Sep. 20, 2001, 86 mg, 0.204 mmol) and DMAP (23 mg, 0.185 mmol), stirred overnight, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 20% 2N NH3 in methanol/dichloromethane to provide the desired product (46 mg, 41%). MS (ESI) m/e 613 (M+H)+; 1H NMR (500 MHz, CD3OD) δ 8.0-6.75 (13H, m), 4.15 (1H, m), 3.59 (2H, t), 3.39 (4H, m), 3.25 (4H, m), 3.16 (2H, t), 2.88 (6H, s), 2.35-2.15 (2H, m).

後処理

  1. temperaturewarmed to room temperature
  2. customprepared
  3. concentrationconcentrated
  4. customThe concentrate was purified by flash column chromatography on silica gel with 20% 2N NH3 in methanol/dichloromethane

出典と根拠

ORDレコード
ord-e01ffd4e2af841c2954170881bffc9b9
出典データセット
uspto-grants-2008_04
特許番号
US07358251B2

反応ノート

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