Trifluoroacetic acid → 2-((R)-1-(2,4-dichlorophenyl)ethylamino)-4-(4-((R)-piperidine-2-carbonyl)piperazin-1-yl)benzonitrile

HRID 75138ノート

反応式

HRID 75138 の反応式
FC(F)(F)C(O)=O.[C:8]([C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:21][CH2:20][N:19]([C:22]([C@H:24]3[CH2:29][CH2:28][CH2:27][CH2:26][N:25]3C(OC(C)(C)C)=O)=[O:23])[CH2:18][CH2:17]2)=[CH:12][C:11]=1[NH:37][C@@H:38]([C:40]1[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][C:41]=1[Cl:47])[CH3:39])#[N:9]>ClCCl>[Cl:47][C:41]1[CH:42]=[C:43]([Cl:46])[CH:44]=[CH:45][C:40]=1[C@H:38]([NH:37][C:11]1[CH:12]=[C:13]([N:16]2[CH2:17][CH2:18][N:19]([C:22]([C@H:24]3[CH2:29][CH2:28][CH2:27][CH2:26][NH:25]3)=[O:23])[CH2:20][CH2:21]2)[CH:14]=[CH:15][C:10]=1[C:8]#[N:9])[CH3:39]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 86689056(R)-t-butyl 2-(4-(4-cyano-3-((R)-1-(2,4-dichlorophenyl)ethylamino)phenyl)piperazine-1-carbonyl)piperidine-1-carboxylate

生成物 1

HCID 715819522-((R)-1-(2,4-dichlorophenyl)ethylamino)-4-(4-((R)-piperidine-2-carbonyl)piperazin-1-yl)benzonitrile収率 75%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Trifluoroacetic acid (0.3 mL) was added to a solution of (R)-t-butyl 2-(4-(4-cyano-3-((R)-1-(2,4-dichlorophenyl)ethylamino)phenyl)piperazine-1-carbonyl)piperidine-1-carboxylate (0.095 g, 0.16 mmol) in dichloromethane (1 mL) at room temperature, and the solution was stirred for 1 h. Excess solvent was removed in vacuo, and the residue was diluted with dichloromethane. The organic layer was neutralized with aqueous saturated sodium bicarbonate solution, and the aqueous layer was further extracted with dichloromethane. The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo to give the title compound as a white solid (0.060 g, 0.12 mmol, 75%). 1H NMR (400 MHz, DMSO-d6) δ 9.0 (br, 1H), 8.62-8.52 (m, 1H), 7.62-7.50 (m, 2H), 7.37 (dd, J=2.2, 8.4 Hz, 1H), 7.05 (d, J=8.8 Hz, 1H), 6.19 (dd, J=2.5, 8.8 Hz, 1H), 5.82 (d, J=2.6 Hz, 1H), 5.68 (br, 1H), 4.86 (br, 1H), 3.70-2.80 (m, 9H), 1.98-1.92 (m, 1H), 1.78-1.58 (m, 4H), 1.50-1.40 (m, 5H); MS: (ES) m/z calculated for C25H30Cl2N5O [M+H]+ 486.2. found 486.

後処理

  1. customExcess solvent was removed in vacuo
  2. additionthe residue was diluted with dichloromethane
  3. extractionthe aqueous layer was further extracted with dichloromethane
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-ed99b1872fc04839acc6446d708eea5d
出典データセット
uspto-grants-2014_09
特許番号
US08835419B2

反応ノート

読み込み中…