Indoline → Adamantan-2-yl-(2,3-dihydro-indol-1-yl)-methanone

HRID 1529247

反応式

HRID 1529247 の反応式
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[C:11]([OH:13])=O)[CH2:8]2.[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.C(O)=O>[CH:3]12[CH2:4][CH:5]3[CH2:6][CH:7]([CH2:8][CH:1]([CH2:10]3)[CH:2]1[C:11]([N:14]1[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][CH2:15]1)=[O:13])[CH2:9]2

参加物

7

反応物 4

HCID 10328IndolineHCID 81531DiisopropylethylamineHCID 3038022-Adamantanecarboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

生成物 1

HCID 71559641Adamantan-2-yl-(2,3-dihydro-indol-1-yl)-methanone

試薬・触媒・溶媒 2

HCID 284Formic Acid溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 24.2 mg (0.134 mmol) adamantane-2-carboxylic acid, 20 mg (0.168 mmol) indoline, 64.7 mg (0.2 mmol) TBTU and 43.4 mg (0.336 mmol) DIPEA in 1 mL DMF was stirred at room temperature overnight. Formic acid was added and the mixture was subjected to column chromatography on reversed phase eluting with a gradient formed from acetonitrile, water and NEt3 to yield after evaporation of the product containing fractions 14.1 mg (30%) of the title compound. MS(m/e): 282.4 (MH+).

後処理

  1. washeluting with a gradient
  2. customformed from acetonitrile, water and NEt3
  3. customto yield
  4. customafter evaporation of the product
  5. additioncontaining fractions 14.1 mg (30%) of the title compound

出典と根拠

ORDレコード
ord-5084855ac78d47e5b4607fbee6b47503
出典データセット
uspto-grants-2015_07
特許番号
US09090615B2

関連ノート

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