4-Chlorobenzenesulfonyl chloride → HCID 22180080, compound

HRID 1795990Notes

Reaction equation

HRID 1795990 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][N:11]2[N:10]=[C:9]1[CH:18]([NH:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1.CCN(CC)CC>C(Cl)(Cl)Cl>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][N:11]2[N:10]=[C:9]1[CH:18]([N:21]([CH2:22][CH2:23][CH2:24][CH3:25])[S:33]([C:30]1[CH:31]=[CH:32][C:27]([Cl:26])=[CH:28][CH:29]=1)(=[O:35])=[O:34])[CH2:19][CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 22180032HCID 22180032, compound

Product 1

HCID 22180080HCID 22180080, compoundYield 7.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
25 °C

Procedure

3-Benzyl-2-(1-butylamino-propyl)-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one (Example 33, 28.0 mg, 0.0828 mmol) in CHCl3 (5 mL) was treated with 4-chloro-benzenesulfonylchloride (52.3 mg, 0.248 mmol) and Et3N (23.0 μL, 0.166 mmol), then stirred for 18 h at 25° C. The mixture was concentrated under vacuum and purified by preparative HPLC using a YMC S10 ODS 20×100 mm column affording the desired compound (3.0 mg, 7.0%) as a colorless film: LC/MS 88% at 4.13 min (ESI+) 513 (M++H).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-3f562df8f75747809bf283fa644b3a97
Source dataset
uspto-grants-2006_04
Patent number
US07030118B2

Reaction notes

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