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1-Hydroxybenzotriazole → 1-Cyclobutyl-4-({1-[(4-methoxycyclohexyl)carbonyl]azetidin-3-yl}carbonyl)-1,4-diazepane

HRID 1402736
ノート
印刷プレビュー

反応式

HRID 1402736 の反応式
[CH3:1][O:2][CH:3]1[CH2:8][CH2:7][CH:6]([C:9]([OH:11])=O)[CH2:5][CH2:4]1.C1C=CC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:46]1[CH2:49][CH:48]([C:50]([N:52]2[CH2:58][CH2:57][CH2:56][N:55]([CH:59]3[CH2:62][CH2:61][CH2:60]3)[CH2:54][CH2:53]2)=[O:51])[CH2:47]1>CN(C=O)C.C(Cl)Cl.C(Cl)Cl>[CH:59]1([N:55]2[CH2:56][CH2:57][CH2:58][N:52]([C:50]([CH:48]3[CH2:47][N:46]([C:9]([CH:6]4[CH2:5][CH2:4][CH:3]([O:2][CH3:1])[CH2:8][CH2:7]4)=[O:11])[CH2:49]3)=[O:51])[CH2:53][CH2:54]2)[CH2:62][CH2:61][CH2:60]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 736153Rac-(1r,4r)-4-methoxycyclohexane-1-carboxylic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 667393581-(Azetidin-3-ylcarbonyl)-4-cyclobutyl-1,4-diazepane

生成物 1

HCID 468516571-Cyclobutyl-4-({1-[(4-methoxycyclohexyl)carbonyl]azetidin-3-yl}carbonyl)-1,4-diazepane
収率 11%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 22350042dichloromethane N,N-dimethylformamide溶媒

実験手順

To a stirred solution of 4-methoxycyclohexane carboxylic acid (20 mg, 0.13 mmol) in DMF/DCM (1:1) (2 ml) was added HOBt (38 mg, 0.28 mmol) and HBTU (96 mg, 0.25 mmol) and the reaction mixture stirred for 15 mins at RT. 1-(Azetidin-3-ylcarbonyl)-4-cyclobutyl-1,4-diazepane (30 mg, 0.13 mmol) in DCM (1 ml) was added and the reaction mixture stirred at RT for 16 hrs. Upon completion, the reaction mixture was evaporated at reduced pressure and purified by silica gel FCC (using DCM/MeOH/NH3; 95:5:0.5 to 90:10:1 as eluent) to give the title compound as colourless oil and as a 1:1 mixture of diastereoisomers by 1H NMR spectroscopy (5.2 mg, 11% yield).

後処理

  1. stirringthe reaction mixture stirred at RT for 16 hrs
  2. customUpon completion, the reaction mixture was evaporated at reduced pressure
  3. custompurified by silica gel FCC (using DCM/MeOH/NH3; 95:5:0.5 to 90:10:1 as eluent)

出典と根拠

ORDレコード
ord-7f6a13ac809341bcacbd30d56d8f8001
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08912176B2

反応ノート

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