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3-(Trifluoromethyl)benzylamine → Tert-butyl 3-(3-((2-(4-((3-(trifluoromethyl)benzyl) carbamoyl) pyridin-2-yl)-4-(piperidin-1-yl)phenyl)carbamoyl)benzylthio)propanoate

HRID 1407956
ノート
印刷プレビュー

反応式

HRID 1407956 の反応式
[C:1]([O:5][C:6](=[O:41])[CH2:7][CH2:8][S:9][CH2:10][C:11]1[CH:12]=[C:13]([CH:38]=[CH:39][CH:40]=1)[C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:19][C:18]=1[C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][N:37]=1)[C:32]([OH:34])=O)=[O:15])([CH3:4])([CH3:3])[CH3:2].[F:42][C:43]([F:53])([F:52])[C:44]1[CH:45]=[C:46]([CH:49]=[CH:50][CH:51]=1)[CH2:47][NH2:48].CCN=C=NCCCN(C)C.Cl>CN(C)C1C=CN=CC=1.ClCCl>[F:42][C:43]([F:52])([F:53])[C:44]1[CH:45]=[C:46]([CH:49]=[CH:50][CH:51]=1)[CH2:47][NH:48][C:32]([C:31]1[CH:35]=[CH:36][N:37]=[C:29]([C:18]2[CH:19]=[C:20]([N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:21]=[CH:22][C:17]=2[NH:16][C:14]([C:13]2[CH:12]=[C:11]([CH:40]=[CH:39][CH:38]=2)[CH2:10][S:9][CH2:8][CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:41])=[O:15])[CH:30]=1)=[O:34]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 759623-(Trifluoromethyl)benzylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 665867222-(2-(3-((3-Tert-butoxy-3-oxopropylthio)methyl)benzamido)-5-(piperidin-1-yl)phenyl)isonicotinic acid

生成物 1

HCID 66586733Tert-butyl 3-(3-((2-(4-((3-(trifluoromethyl)benzyl) carbamoyl) pyridin-2-yl)-4-(piperidin-1-yl)phenyl)carbamoyl)benzylthio)propanoate

試薬・触媒・溶媒 2

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

実験手順

Into a 50 mL round bottom flask, was placed 2-(2-(3-((3-tert-butoxy-3-oxopropylthio)methyl)benzamido)-5-(piperidin-1-yl)phenyl)isonicotinic acid (220 mg, 0.38 mmol, 1.00 equiv), 3-(trifluoromethyl)benzylamine (134 mg, 0.77 mmol, 2.00 equiv), EDC.HCl (124 mg, 0.63 mmol, 1.65 equiv), 4-dimethylaminopyridine (76 mg, 0.62 mmol, 1.63 equiv), and dichloromethane (10 mL). The resulting solution was stirred overnight at room temperature. The reaction progress was monitored by LCMS. The resulting mixture was washed with 5×30 mL of aqueous NH4Cl. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 360 mg (90%) of tert-butyl 3-(3-((2-(4-((3-(trifluoromethyl)benzyl)carbamoyl)pyridin-2-yl)-4-(piperidin-1-yl)phenyl)carbamoyl)benzylthio)propanoate as yellow oil.

後処理

  1. customInto a 50 mL round bottom flask, was placed
  2. washThe resulting mixture was washed with 5×30 mL of aqueous NH4Cl
  3. dry with materialThe mixture was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThis resulted in 360 mg (90%) of tert-butyl 3-(3-((2-(4-((3-(trifluoromethyl)benzyl)carbamoyl)pyridin-2-yl)-4-(piperidin-1-yl)phenyl)carbamoyl)benzylthio)propanoate as yellow oil

出典と根拠

ORDレコード
ord-3d8440882f3d462ba7f86ac47b4df901
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08916569B2

反応ノート

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