Formic acid methanol → 4-[2-(5-Chlorothiophen-2-yl)-ethenesulfonyl]-1-(2-pyrrolo[3 2-c]pyridin-1-ylethyl)-piperazin-2-one

HRID 1433001노트

반응식

HRID 1433001 반응식
C(OC([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][N:19]2[C:27]3[CH:26]=[CH:25][N:24]=[CH:23][C:22]=3[CH:21]=[CH:20]2)[C:13](=[O:28])[CH2:12]1)=O)C1C=CC=CC=1.C(O)=O.CO.[Cl:34][C:35]1[S:39][C:38]([CH:40]=[CH:41][S:42](Cl)(=[O:44])=[O:43])=[CH:37][CH:36]=1>[Pd].C(#N)C>[Cl:34][C:35]1[S:39][C:38]([CH:40]=[CH:41][S:42]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][N:19]3[C:27]4[CH:26]=[CH:25][N:24]=[CH:23][C:22]=4[CH:21]=[CH:20]3)[C:13](=[O:28])[CH2:12]2)(=[O:44])=[O:43])=[CH:37][CH:36]=1

참가 물질

6

반응물 3

HCID 18963719Formic acid methanolHCID 540369894-(Benzyloxycarbonyl)-1-(2-pyrrolo[3,2-c]pyridin-1-ylethyl)-piperazin-2-oneHCID 544630642-(5-Chlorothiophen-2-yl)ethenesulfonyl chloride

생성물 1

HCID 537426124-[2-(5-Chlorothiophen-2-yl)-ethenesulfonyl]-1-(2-pyrrolo[3 2-c]pyridin-1-ylethyl)-piperazin-2-one

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 6342Acetonitrile용매

실험 절차

4-(Benzyloxycarbonyl)-1-(2-pyrrolo[3,2-c]pyridin-1-ylethyl)-piperazin-2-one (0.028 g, 0.074 mmol), EXAMPLE 98, is treated with 4% HCO2H/MeOH (5 mL) and a catalytic amount of Pd black for 5 minutes. The reaction mixture is filtered washed with methanol and the filtrate is concentrated to a residue. The residue is treated with acetonitrile (3 mL) excess N-methylmorpholine (0.04 mL) and 2-(5-chlorothiophen-2-yl)ethene-sulfonyl chloride (0.018 g, 0.074 mmol), EXAMPLE 3, and processed as usual (EXAMPLE 719). Further chromatographic purification (NH4OH/MeOH/CH2Cl2: 1/4/95) yields the title compound: MS m/z 451, 453 (M+H); 1H NMR (CDCl3, 300 MHz) δ8.93 (bs, 1H), 8.24 (bs, 1H), 7.41 (d, 1H), 7.23 (d, 1H), 7.14 (m, 2H), 6.94 (d, 1H), 6.68 (d. 1H), 6.18 (d, 1H), 4.43 (t, 2H), 3.67 (t, 2H), 2.88 (t, 2H), 2.66 (t, 2H).

후처리

  1. filtrationThe reaction mixture is filtered
  2. washwashed with methanol
  3. concentrationthe filtrate is concentrated to a residue
  4. customFurther chromatographic purification (NH4OH/MeOH/CH2Cl2: 1/4/95)

출처 및 근거

ORD 기록
ord-41fb93e1b432451d961722e317f76724
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612075B2

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