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Isopropylamine → 5-(3-iodo-1-tosyl-1H-indol-5-yl)-N-isopropyl-1,3,4-oxadiazol-2-amine

HRID 634209
ノート
印刷プレビュー

反応式

HRID 634209 の反応式
F[P-](F)(F)(F)(F)F.[N:8]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:12]2[CH:13]=CC=C[C:11]=2N=N1.[I:28][C:29]1[C:37]2[C:32](=[CH:33][CH:34]=[C:35]([C:38]3[O:42][C:41](=O)[NH:40][N:39]=3)[CH:36]=2)[N:31]([S:44]([C:47]2[CH:53]=[CH:52][C:50]([CH3:51])=[CH:49][CH:48]=2)(=[O:46])=[O:45])[CH:30]=1.CC(N)C.C(N(C(C)C)CC)(C)C>CN(C=O)C.O>[I:28][C:29]1[C:37]2[C:32](=[CH:33][CH:34]=[C:35]([C:38]3[O:42][C:41]([NH:8][CH:12]([CH3:13])[CH3:11])=[N:40][N:39]=3)[CH:36]=2)[N:31]([S:44]([C:47]2[CH:48]=[CH:49][C:50]([CH3:51])=[CH:52][CH:53]=2)(=[O:45])=[O:46])[CH:30]=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 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 683283805-(3-iodo-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2(3H)-one

生成物 1

HCID 683289275-(3-iodo-1-tosyl-1H-indol-5-yl)-N-isopropyl-1,3,4-oxadiazol-2-amine収率 73.4%

試薬・触媒・溶媒

2
HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

BOP (253 mg, 0.571 mmol) was added to a stirred mixture of 5-(3-iodo-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2(3H)-one (250 mg, 0.519 mmol), propan-2-amine (0.13 mL, 1.56 mmol) and diisopropylethylamine (0.18 mL, 1.04 mmol) in DMF (1.5 mL). The reaction was stirred at RT for 14 h then diluted with water and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4 and concentrated. Purification on the ISCO (12 g column, 20-70% EtOAc in Hex) afforded 5-(3-iodo-1-tosyl-1H-indol-5-yl)-N-isopropyl-1,3,4-oxadiazol-2-amine (199 mg, 73%) as a white amorphous solid. MS (ESI, pos. ion) m/z: 523.0 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 8.02 (1H, d, J=8.6 Hz), 7.95 (1H, d, J=8.4 Hz), 7.86 (1H, s), 7.76-7.82 (2H, m), 7.71-7.76 (1H, m), 7.28 (2H, s), 4.54 (1H, d, J=7.6 Hz), 3.94-4.05 (1H, m), 2.37 (3H, s), 1.34 (6H, d, J=6.5 Hz).

後処理

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customPurification on the ISCO (12 g column, 20-70% EtOAc in Hex)

出典と根拠

ORDレコード
ord-d0df176017b14c41bb5b0956a94a6a0d
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09321756B2

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