Diisopropylethylamine → HCID 18617839、化合物

HRID 1264239ノート

反応式

HRID 1264239 の反応式
[O:1]=[C:2]1[NH:7][CH2:6][CH:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[NH2:17][CH2:18][CH2:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][CH:24]=[C:23]2[C:29]#[N:30].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(O)(C(F)(F)F)=O.O.C(O)(C(F)(F)F)=O.C(#N)C>CN(C=O)C>[C:29]([C:23]1[C:22]2[C:26](=[CH:27][CH:28]=[C:20]([CH2:19][CH2:18][NH:17][C:12](=[O:14])[C:11]3[CH:10]=[CH:9][C:8]([CH:5]4[CH2:4][CH2:3][C:2](=[O:1])[NH:7][CH2:6]4)=[CH:16][CH:15]=3)[CH:21]=2)[NH:25][CH:24]=1)#[N:30]

参加物

8

反応物 6

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11217658HCID 11217658、化合物HCID 18617602HCID 18617602、化合物HCID 21924481TFA acetonitrileHCID 22392675Trifluoroacetic acid water

生成物 1

HCID 18617839HCID 18617839、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

4-(6-Oxo-piperidin-3-yl)-benzoic acid (190 mg, 0.87 mmol, reference example 65) and 5-(2-amino-ethyl)-1H-indole-3-carbonitrile (161 mg, 0.87 mmol, reference example 2) is dissolved in anhydrous DMF (3 mL). To this solution is added diisoproplyethylamine (330 μl, 1.9 mmol), followed by HBTU (330 mg, 0.87 mmol) and allowed to stir at room temperature overnight (16 hours). The product is isolated by Reverse-Phase chromatography of the crude reaction mixture (Dynamax C-18 60 A (5×30 cm), 50 ml/min, λ@ 220 nm, 10-70% B in 15 minutes, A: 0.1% TFA/water, B: 0.1% TFA/acetonitrile). 1H NMR (300 MHz, DMSO) δ 1.94 (m, 2H), 2.26 (m, 2H), 2.92 (t, J=7.1, 2H), 3.19 (m, 1H), 3.48 (m, 2H), 3.46 (m, 2H), 7.13 (d, J=8.4, 1H), 7.15 (d, J=1.4, 2H), 7.36 (d, J=8.3, 2H), 7.43 (d, J=8.5, 1H), 7.46 (s, 1H), 7.55 (d, J=2.5, 1H), 7.73 (d, J=8.3, 2H), 8.17 (d, J=3.0, 1H), 8.47 (t, J=5.5, 1H). MS (Ion spray) m/z 387 (M+H)+.

後処理

  1. customThe product is isolated by Reverse-Phase chromatography of the crude
  2. customreaction mixture (Dynamax C-18 60 A (5×30 cm), 50 ml/min, λ@ 220 nm, 10-70% B in 15 minutes

出典と根拠

ORDレコード
ord-4fcf2a382dfd4ceeba68e80d9cb7c222
出典データセット
uspto-grants-2003_04
特許番号
US06541505B1

反応ノート

読み込み中…