1-Hydroxybenzotriazole → 5-(2,6-Dichloro-phenylmethanesulfonyl)-3-[1-{4-[2-(4-hydroxy-piperidin-1-yl)-2-oxo-ethyl]-3,5-dimethyl-1h-pyrrol-2-yl}-meth-(z)-ylidene]-1,3-dihydro-indol-2-one

HRID 1359721노트

반응식

HRID 1359721 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][S:10]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])/[C:16]/2=[CH:23]\[C:24]1[NH:28][C:27]([CH3:29])=[C:26]([CH2:30][C:31]([OH:33])=O)[C:25]=1[CH3:34])(=[O:12])=[O:11].[CH:35]1[CH:36]=[CH:37]C2N(O)N=[N:41][C:39]=2[CH:40]=1.CCN=C=NCCCN(C)C.Cl.N1([OH:63])CCNCC1>CN(C=O)C>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[CH2:9][S:10]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17](=[O:22])/[C:16]/2=[CH:23]\[C:24]1[NH:28][C:27]([CH3:29])=[C:26]([CH2:30][C:31]([N:41]2[CH2:37][CH2:36][CH:35]([OH:63])[CH2:40][CH2:39]2)=[O:33])[C:25]=1[CH3:34])(=[O:12])=[O:11]

참가 물질

6

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12463393Piperazin-1-olHCID 59077497HCID 59077497, 화합물

생성물 1

HCID 590775885-(2,6-Dichloro-phenylmethanesulfonyl)-3-[1-{4-[2-(4-hydroxy-piperidin-1-yl)-2-oxo-ethyl]-3,5-dimethyl-1h-pyrrol-2-yl}-meth-(z)-ylidene]-1,3-dihydro-indol-2-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a mixture of {5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrol-3-yl}-acetic acid (100 mg, 0.19 mmol), HOBt (3 mg, 0.1 eq.), EDAC.HCl (44 mg, 1.2 eq.) and piperazin-1-ol (21 mg, 1.1 eq.) in DMF (2 mL) at rt was added TEA (0.067 mL, 2.5 eq.). After stirring at rt for 7 days, the reaction was concentrated, diluted with DCM (10 mL) and methanol (0.5 mL) and then mixed with solid sodium bicarbonate. After stirring at rt for 15 mins, the suspension was loaded onto a silica gel column to give the titled compound as an orange solid.

후처리

  1. concentrationthe reaction was concentrated
  2. additiondiluted with DCM (10 mL) and methanol (0.5 mL)
  3. additionmixed with solid sodium bicarbonate
  4. stirringAfter stirring at rt for 15 mins

출처 및 근거

ORD 기록
ord-23962487b0134d0c8b77b48c5d9f29ed
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06599902B2

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