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

HRID 1433001Notes

Reaction equation

HRID 1433001 reaction equation
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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6342AcetonitrileSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-41fb93e1b432451d961722e317f76724
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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