4-Toluenesulfonyl chloride → HCID 86612117, compound

HRID 2114826Notes

Reaction equation

HRID 2114826 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]3[C:13]4[CH2:20][CH2:19][NH:18][C:17](=[O:21])[C:14]=4[C:15]([OH:16])=[C:9]3[C:8]2=[O:22])=[CH:4][CH:3]=1.C(N([CH2:30][CH3:31])CC)C.[C:32]1(C)[CH:37]=C[C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=1>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]3[C:13]4[CH2:20][CH2:19][NH:18][C:17](=[O:21])[C:14]=4[C:15]([O:16][S:38]([C:35]4[C:30]([CH3:31])=[CH:37][CH:32]=[CH:33][CH:34]=4)(=[O:40])=[O:39])=[C:9]3[C:8]2=[O:22])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 54692340HCID 54692340, compound

Product 1

HCID 86612117HCID 86612117, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-(4-fluorobenzyl)-10-hydroxy-3,4,7,8-tetrahydropyrido-[3′,4′:4,5]pyrrolo[1,2-a]pyrazine-1,9(2H,6H)-dione (1.0 g, 3.0 mmol) and triethylamine (0.64 mL, 4.6 mmol) in dichloromethane (30 mL), p-toluenesulfonyl chloride (0.64 g, 3.34 mmol) was added. The reaction mixture was stirred at rt overnight and concentrated under vacuum. The residue was subjected to reverse phase preparative HPLC purification. Collection and lyophilization of appropriate fractions provided the titled compounds.

Workup

  1. concentrationconcentrated under vacuum
  2. customphase preparative HPLC purification
  3. customCollection and lyophilization of appropriate fractions

Sources & evidence

ORD record
ord-9c3f99f9537747f2b01fdb01f3cfdcb8
Source dataset
uspto-grants-2008_10
Patent number
US07435735B2

Reaction notes

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