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Nitrogen → Arq-621

HRID 1517351
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HRID 1517351 반응식
[Cl:1][C:2]1[C:3]([F:48])=[C:4]([CH:45]=[CH:46][CH:47]=1)[C:5]([N:7]([C@@H:22]([C:26]1[N:35]([NH:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:34](=[O:43])[C:33]2[C:28](=[CH:29][C:30]([Cl:44])=[CH:31][CH:32]=2)[N:27]=1)[CH2:23][C:24]#[CH:25])[CH2:8][CH2:9][CH2:10][N:11]1C(=O)C2C(=CC=CC=2)C1=O)=[O:6].N#N.NN>CO>[NH2:11][CH2:10][CH2:9][CH2:8][N:7]([C@@H:22]([C:26]1[N:35]([NH:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:34](=[O:43])[C:33]2[C:28](=[CH:29][C:30]([Cl:44])=[CH:31][CH:32]=2)[N:27]=1)[CH2:23][C:24]#[CH:25])[C:5](=[O:6])[C:4]1[CH:45]=[CH:46][CH:47]=[C:2]([Cl:1])[C:3]=1[F:48]
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참가 물질

5

반응물 3

HCID 947NitrogenHCID 9321HydrazineHCID 576954593-chloro-N-[(R)-1-(7-chloro-4-oxo-3-phenylamino-3,4-dihydro-quinazolin-2-yl)-but-3-ynyl]-N-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)propyl]-2-fluoro-benzamide

생성물 1

HCID 25110841Arq-621수율 91%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of (R)-3-chloro-N-[1-(7-chloro-4-oxo-3-phenylamino-3,4-dihydro-quinazolin-2-yl)-but-3-ynyl]-N-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propyl]-2-fluoro-benzamide (1.13 g, 1.65 mmol) in methanol (10 ml) and the solution was purged with N2. To this solution was added hydrazine (110 μl). The mixture was then stirred at room temperature and the reaction progress was monitored by HPLC/MS. The reaction mixture was then filtered and solvent was removed from the filtrate. The residue was purified by flash column to afford N-(3-amino-propyl)-3-chloro-N-[(R)-1-(7-chloro-4-oxo-3-phenylamino-3,4-dihydro-quinazolin-2-yl)-but-3-ynyl]-2-fluoro-benzamide (708 mg, 91%) as off-white solid, M.p. 101-103° C. LCMS: m/e 552 [M+H]. 1H NMR (CDCl3): δ 8.13 (d, J=8.8 Hz, 1H), 7.83 (s, 1H), 7.45 (dd, J=4.8 and 2.0 Hz, 1H), 7.32 (m, 1H), 7.22 (t, J=8.0 Hz, 1H), 7.15 (t, J=8.0 Hz, 1H), 7.05 (t, J=8.0 Hz, 1H), 6.95 (m, 1H), 6.84 (t, J=7.2 Hz, 1H), 6.72 (d, J=7.2 Hz, 1H), 6.48 (d, J=7.2 Hz 1H), 3.62 (m, 1H), 3.48 (m, 1H), 3.28 (br, 1H), 3.14 (m, 1H), 3.02 (br, 1H), 2.59 (m, 2H), 2.30 (br, 1H), 2.02 (t, 2.4 Hz, 1H), 1.36 (m, 2H).

후처리

  1. filtrationThe reaction mixture was then filtered
  2. customsolvent was removed from the filtrate
  3. customThe residue was purified by flash column

출처 및 근거

ORD 기록
ord-51d7d0a390044e909766ada919e7e8d7
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08232285B2

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