Diisopropylethylamine → 1-{4-[4-(1H-indazol-3-yl)-1H-1,2,3-triazol-1-yl]benzoyl}pyrrolidin-3-ol

HRID 1520057ノート

反応式

HRID 1520057 の反応式
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]([C:32]2[N:33]=[N:34][N:35]([C:37]3[CH:45]=[CH:44][C:40]([C:41]([OH:43])=O)=[CH:39][CH:38]=3)[CH:36]=2)=[N:24]1.CCN(C(C)C)C(C)C.[NH:55]1[CH2:59][CH2:58][CH:57]([OH:60])[CH2:56]1>CN(C=O)C.C(Cl)Cl>[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]([C:32]2[N:33]=[N:34][N:35]([C:37]3[CH:45]=[CH:44][C:40]([C:41]([N:55]4[CH2:59][CH2:58][CH:57]([OH:60])[CH2:56]4)=[O:43])=[CH:39][CH:38]=3)[CH:36]=2)=[N:24]1

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 982104-HydroxypyrrolidineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 679811434-[4-(1H-indazol-3-yl)-1H-1,2,3-triazol-1-yl]benzoic acid

生成物 1

HCID 679818451-{4-[4-(1H-indazol-3-yl)-1H-1,2,3-triazol-1-yl]benzoyl}pyrrolidin-3-ol

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

A solution of TBTU (137 mg; 0.33 mmol; 1.3 eq.) and 4-[4-(1H-indazol-3-yl)-1H-1,2,3-triazol-1-yl]benzoic acid (100 mg; 0.33 mmol; 1.0 eq.) in DMF (2 mL) was stirred for 1 h at RT before the addition of DIEA (111 μl; 0.66 mmol; 2.0 eq.) and 3-pyrrolidinol (43 mg; 0.49 mmol.; 1.5 eq.). The reaction mixture was stirred at RT overnight. It was then diluted with DCM and washed with an aqueous saturated solution of NaHCO3. Organic phase was dried over magnesium sulfate, filtered and concentrated. The crude was purified by preparative HPLC to afford the title compound as a yellow solid. 1H NMR (300 Mz, DMSO-d6) δ 13.38 (s, 1H), 9.41 (s, 1H), 8.37 (d, J=8.1 Hz, 1H), 8.15 (d, J=8.7 Hz, 2H), 7.78 (dd, J=3.2, 8.6 Hz, 2H), 7.62 (d, J=8.4 Hz, 1H), 7.51-7.39 (m, 1H), 7.27 (t, J=7.1 Hz, 1H), 4.32 (brd, J=26.0 Hz, 1H), 3.76-3.54 (m, 2H), 3.54-3.20 (m, 3H), 2.06-1.75 (m, 2H). HPLC (Condition A): Rt 2.58 min (purity 96.7%). MS (ESI+): 375.2, MS (ESI−): 373.2.

後処理

  1. washwashed with an aqueous saturated solution of NaHCO3
  2. dry with materialOrganic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude was purified by preparative HPLC

出典と根拠

ORDレコード
ord-3b6bf45efd1c4ae79b98c30569ab2b01
出典データセット
uspto-grants-2015_07
特許番号
US09073892B2

反応ノート

読み込み中…