Triethylamine → 2-{4-[2-(5-Chloro-thiophen-2-yl)-ethenesulfonyl]-2-oxopiperazin-1-ylmethyl}pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester

HRID 1432948Notes

Reaction equation

HRID 1432948 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[CH:14][N:13]=[CH:12][C:11]=2[CH:10]=[C:9]1[CH2:17][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][C:19]1=[O:24])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Cl:32][C:33]1[S:37][C:36]([CH:38]=[CH:39][S:40](Cl)(=[O:42])=[O:41])=[CH:35][CH:34]=1>CC#N>[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[CH:14][N:13]=[CH:12][C:11]=2[CH:10]=[C:9]1[CH2:17][N:18]1[CH2:23][CH2:22][N:21]([S:40]([CH:39]=[CH:38][C:36]2[S:37][C:33]([Cl:32])=[CH:34][CH:35]=2)(=[O:42])=[O:41])[CH2:20][C:19]1=[O:24])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 544278362-(2-Oxo-piperazin-1-ylmethyl)-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl esterHCID 544630642-(5-Chlorothiophen-2-yl)ethenesulfonyl chloride

Product 1

HCID 690271762-{4-[2-(5-Chloro-thiophen-2-yl)-ethenesulfonyl]-2-oxopiperazin-1-ylmethyl}pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(2-oxopiperazin-1-ylmethyl)pyrrolo[3,2-c]pyridin-1-carboxylic acid tert-butyl ester (0.71 g, 2.1 mmol), EXAMPLE 69, in CH3CN (7 mL) is added triethylamine (0.60 mL, 4.3 mmol) followed by 2-(5-chloro-thiophen-2-yl)-ethenesulfonyl chloride, EXAMPLE 3, (0.57 g, 2.1 mmol). The mixture is stirred overnight, then concentrated to dryness. The residue is diluted with CH2Cl2 and washed with saturated sodium bicarbonate and brine. The organic layer is dried over MgSO4, filtered and concentrated in vacuo to give the title compound (1.2 g, 2.1 mmol) as a light yellow solid. The crude material can be used in the subsequent step without further purification. 1H NMR (CDCl3, 300 MHz) δ8.80 (s, 1H), 8.42 (d, 1H), 7.88 (d, 1H), 7.55 (d, 1H), 7.14 (d, 1H), 6.98 (d, 1H), 6.41 (s, 1H), 6.36 (d, 1H), 5.00 (s, 2H), 3.98 (s, 2H), 3.61 (m, 4H), 1.71 (s, 9H). Ion spray MS, [M+H]+=537, 539, Cl pattern.

Workup

  1. concentrationconcentrated to dryness
  2. additionThe residue is diluted with CH2Cl2
  3. washwashed with saturated sodium bicarbonate and brine
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3dc99c07b5344021bc5ee19cef526c2e
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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