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Methanol → HCID 178481494、化合物

HRID 447996
ノート
印刷プレビュー

反応式

HRID 447996 の反応式
[C:1]1([C:7]2[CH:12]=[C:11]([CH:13]3[CH2:18][C:17](=[O:19])[N:16]([CH3:20])[C:15](=[O:21])[CH2:14]3)[CH:10]=[CH:9][C:8]=2[NH:22][C:23]([C:25]2[N:26](COCC[Si](C)(C)C)[CH:27]=[C:28]([C:30]#[N:31])[N:29]=2)=[O:24])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.CO.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]1([C:7]2[CH:12]=[C:11]([CH:13]3[CH2:18][C:17](=[O:19])[N:16]([CH3:20])[C:15](=[O:21])[CH2:14]3)[CH:10]=[CH:9][C:8]=2[NH:22][C:23]([C:25]2[NH:26][CH:27]=[C:28]([C:30]#[N:31])[N:29]=2)=[O:24])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 887Methanol2 回HCID 6422Trifluoroacetic acidHCID 597712494-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(1-methyl-2,6-dioxo-piperidin-4-yl)-phenyl]-amide

生成物 1

HCID 178481494HCID 178481494、化合物収率 8.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane
溶媒

実験手順

A solution of 130 mg (0.237 mmol) of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid[2-cyclohex-1-enyl-4-(1-methyl-2,6-dioxo-piperidin-4-yl)-phenyl]-amide (as prepared in the previous step) in CH2Cl2 (10 mL) was treated with MeOH (200 μL) and TFA (3 mL) at RT for 1.25 h. MeOH (30 mL) was added, the mixture was concentrated to half volume, MeOH (20 mL) was added, and the solvents were removed completely in vacuo at <35° C. Silica gel chromatography of the residue on a 50-g Varian MegaBond Elut SPE column with 25-50% EtOAc-hexane and by RP-HPLC (C18) with 10-80% CH3CN in 0.1% TFA/H2O over 30 min afforded 8.0 mg (8%) of the title compound as a white solid: 1H-NMR (CD3OD; 400 MHz): δ 8.19 (d, 1H, J=8.4 Hz), 8.03 (s, 1H), 7.24 (dd, 1H, J=8.4, 2.4 Hz), 7.16 (d, 1H, J=2.4 Hz), 5.87-5.82 (m, 1H), 3.47-3.37 (m, 1H), 3.16 (s, 3H), 2.96-2.91 (m, 4H), 2.33-2.25 (m, 4H), 1.92-1.77 (m, 4H). Mass spectrum (ESI, m/z): Calcd. for C23H23N5O3, 418.2 (M+H), found 418.1.

後処理

  1. concentrationthe mixture was concentrated to half volume, MeOH (20 mL)
  2. additionwas added
  3. customthe solvents were removed completely in vacuo at <35° C

出典と根拠

ORDレコード
ord-ccfd1d2575e449bda44270a138c6a95f
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08481564B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート