4-Methylmorpholine → (4aR,7aS)-1-[(4-fluorophenyl)methyl]-4-hydroxy-3-(7-iodo-1,1-dioxo-4H-1$l^{6},2,4-benzothiadiazin-3-yl)-5,6,7,7a-tetrahydro-4aH-cyclopenta[b]pyridin-2-one

HRID 731344노트

반응식

HRID 731344 반응식
[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][NH:7][C@H:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[C:13]([O:15]C)=O)=[CH:4][CH:3]=1.[I:19][C:20]1[CH:35]=[CH:34][C:23]2[NH:24][C:25]([CH2:30][C:31](O)=[O:32])=[N:26][S:27](=[O:29])(=[O:28])[C:22]=2[CH:21]=1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C@@H:8]3[C@@H:9]([CH2:10][CH2:11][CH2:12]3)[C:13]([OH:15])=[C:30]([C:25]3[NH:24][C:23]4[CH:34]=[CH:35][C:20]([I:19])=[CH:21][C:22]=4[S:27](=[O:28])(=[O:29])[N:26]=3)[C:31]2=[O:32])=[CH:17][CH:18]=1

참가 물질

7

반응물 4

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57832628methyl (1R,2S)-2-(4-fluoro-benzylamino)-cyclopentanecarboxylateHCID 59853574(7-Iodo-1,1-dioxo-1,4-dihydro-1lambda6-benzo[1,2,4]thiadiazin-3-yl)-acetic acid

생성물 1

HCID 135955738(4aR,7aS)-1-[(4-fluorophenyl)methyl]-4-hydroxy-3-(7-iodo-1,1-dioxo-4H-1$l^{6},2,4-benzothiadiazin-3-yl)-5,6,7,7a-tetrahydro-4aH-cyclopenta[b]pyridin-2-one

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
25 °C

실험 절차

To a stirred solution of methyl (1R,2S)-2-(4-fluoro-benzylamino)-cyclopentanecarboxylate (2.50 g, 10 mmol) in anhydrous N,N-dimethylformamide (25 mL) under a nitrogen atmosphere, (7-iodo-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-acetic acid (prepared as described in Example 24b, 3.66 g, 10 mmol), N-methylmorpholine (2.20 mL, 20 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.92 g, 10 mmol) were added sequentially. After stirring at 25° C. for 16 h, the reaction mixture was diluted with ethyl acetate, washed with a 1.0 M aqueous hydrochloric acid solution and saturated aqueous brine solution, dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo to afford the crude amide intermediate.

후처리

  1. washwashed with a 1.0 M aqueous hydrochloric acid solution and saturated aqueous brine solution
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-bb830a6631cf4519b24ca2aa91b30bfe
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582626B2

반응 노트

불러오는 중…