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Diisopropylethylamine → {2-Methoxy-4-[4-(1-methyl-piperidin-4-yl)-piperazin-1-yl]-phenyl}-[7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-amine

HRID 1261960
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HRID 1261960 반응식
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N:9]2[CH2:14][CH2:13][N:12]([CH:15]3[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]3)[CH2:11][CH2:10]2)[CH:6]=[CH:5][C:4]=1[NH2:22].CS([C:26]1[N:31]=[CH:30][C:29]2=[CH:32][CH:33]=[C:34]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[O:41][CH3:42])[N:28]2[N:27]=1)=O.C(N(CC)C(C)C)(C)C>COCCO.CO>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N:9]2[CH2:14][CH2:13][N:12]([CH:15]3[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]3)[CH2:11][CH2:10]2)[CH:6]=[CH:5][C:4]=1[NH:22][C:26]1[N:31]=[CH:30][C:29]2=[CH:32][CH:33]=[C:34]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[O:41][CH3:42])[N:28]2[N:27]=1
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참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 574161562-Methoxy-4-(4-(1-methylpiperidin-4-yl)piperazin-1-yl)anilineHCID 667107912-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine

생성물 1

HCID 66710680{2-Methoxy-4-[4-(1-methyl-piperidin-4-yl)-piperazin-1-yl]-phenyl}-[7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-amine수율 53.6%

시약·촉매·용매 2

HCID 887
Methanol
용매
HCID 80192-Methoxyethanol용매

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온도
180 °C

실험 절차

A solution of 2-methoxy-4-[4-(1-methyl-piperidin-4-yl)-piperazin-1-yl]-phenylamine (140 mg, 0.45 mmol) and 2-methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine (65 mg, 0.23 mmol) in 2-methoxyethanol (0.50 mL) was treated with N,N-diisopropylethylamine (59 uL, 0.34 mmol). The reaction was heated under microwave conditions at 300 watts at 180° C. for 90 minutes. The mixture was diluted with methanol (10 mL), filtered and concentrated. The residue was purified by preparative RP-HPLC to give 65 mg of an amber amorphous powder. MS=528 (M-TFA+H); NMR (DMSO-d6, ppm): 10.15 (s, 1H), 9.83 (s, 1H), 8.92 (s, 1H), 7.92 (d, J=9 Hz, 1H), 7.85 (d, J=8 Hz, 1H), 7.57 (s, 1H), 7.43 (t, J=8 Hz, 1H), 7.19 (d, J=8 Hz, 1H), 7.09 (t, J=8 Hz, 1H), 6.95 (q, J=5 Hz, 14 Hz, 1H), 6.73 (s, 1H), 6.45 (d, J=9 Hz, 1H), 3.87 (s, 3H), 3.80 (s, 3H), 3.61 (m, 4H), 3.48 (m, 2H), 3.22 (m, 2H), 3.00 (m, 4H), 2.80 (s, 3H), 2.67 (m, 1H), 2.37 (m, 2H), 1.88 (m, 2H).

후처리

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe residue was purified by preparative RP-HPLC

출처 및 근거

ORD 기록
ord-5fd5ff6bdb6b4277a39e682859fc46b3
출처 데이터셋
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08471005B2

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