Triethylamine → HCID 59577481、化合物

HRID 1947536ノート

反応式

HRID 1947536 の反応式
Cl.[N:2]1([CH2:8][C:9]2[C:13]3[CH:14]=[CH:15][C:16]([O:18][C:19]4[S:20][C:21]5[C:22]([N:27]=4)=[N:23][CH:24]=[CH:25][CH:26]=5)=[CH:17][C:12]=3[O:11][CH:10]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.CCN(CC)CC.C[Si]([N:39]=[C:40]=[O:41])(C)C>C(Cl)Cl>[S:20]1[C:21]2[C:22](=[N:23][CH:24]=[CH:25][CH:26]=2)[N:27]=[C:19]1[O:18][C:16]1[CH:15]=[CH:14][C:13]2[C:9]([CH2:8][N:2]3[CH2:7][CH2:6][N:5]([C:40]([NH2:39])=[O:41])[CH2:4][CH2:3]3)=[CH:10][O:11][C:12]=2[CH:17]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 70696Trimethylsilyl isocyanateHCID 68769983HCID 68769983、化合物

生成物 1

HCID 59577481HCID 59577481、化合物収率 44.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a suspension of 2-(3-piperazin-1-ylmethyl-benzofuran-6-yloxy)-thiazolo[4,5-b]pyridine hydrochloride (122 mg, 0.30 mmol) in DCM (3 mL) was added Et3N (0.21 mL, 1.51 mmol) and the reaction mixture was stirred (rt, 15 min). The resulting solution was treated with trimethylsilyl isocyanate (0.14 mL, 0.91 mmol) and stirred (rt, 4 h). The reaction mixture was concentrated in vacuo and the resulting residue was purified by reverse phase HPLC to afford the title compound as a white solid (55 mg, 44%). MS (ESI): mass calcd. for C20H19N5O3S, 409.47; m/z found, 410.0 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.56 (dd, J=4.8, 1.6, 1H), 8.02 (dd, J=7.9, 1.6, 1H), 7.77 (d, J=8.5, 1H), 7.59 (d, J=1.9, 2H), 7.29 (dd, J=8.5, 2.1, 1H), 7.21 (dd, J=7.9, 4.8, 1H), 4.43 (s, 2H), 3.66 (d, J=0.7, 2H), 3.47-3.36 (m, 4H), 2.55-2.46 (m, 4H).

後処理

  1. stirringstirred (rt, 4 h)
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe resulting residue was purified by reverse phase HPLC

出典と根拠

ORDレコード
ord-2bb85cb018b2499c845e2b56915ff8b0
出典データセット
uspto-grants-2013_03
特許番号
US08399465B2

反応ノート

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