Triethylamine → HCID 59577481, 화합물

HRID 1947536노트

반응식

HRID 1947536 반응식
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

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 70696Trimethylsilyl isocyanateHCID 68769983HCID 68769983, 화합물

생성물 1

HCID 59577481HCID 59577481, 화합물수율 44.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-2bb85cb018b2499c845e2b56915ff8b0
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399465B2

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