Benzenesulfonyl chloride → HCID 86592477, compound

HRID 1766276Notes

Reaction equation

HRID 1766276 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[C:16]3[CH:15]=[C:14]([OH:17])[CH:13]=[CH:12][C:11]=3[N:10]3[CH2:18][CH2:19][CH2:20][C:9]=23)[CH2:4][CH2:3]1.[OH-].[Na+].[C:23]1([S:29]([Cl:32])(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[ClH:32].[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[C:16]3[CH:15]=[C:14]([O:17][S:29]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)(=[O:31])=[O:30])[CH:13]=[CH:12][C:11]=3[N:10]3[CH2:18][CH2:19][CH2:20][C:9]=23)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 17980126HCID 17980126, compound

Product 1

HCID 86592477HCID 86592477, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By a method similar to Example 31, using 9-(1-methylpiperidin-4-yl)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-ol (135 mg, 0.5 mmol), NaOH (3.25 mL, 0.65 mmol, 0.2 N), benzenesulfonyl chloride (99 mg, 0.564 mmol), and THF (1.5 mL) gave a crude residue which was purified by PCTLC (silica gel GF rotor; 95:5 CHCl3:2M NH3 in MeOH) and the hydrochloride was formed in EtOAc affording 196 mg (88%) of the title compound as an off-white powder: mp=202-204° C.; MS (ES+): m/e 411.0 (M+1); Calculated for C23H26N2O3S.HCl: C, 61.80; H, 6.09; N, 6.27. Found: C, 61.49; H, 6.10; N, 6.27.

Workup

  1. customgave a crude residue which
  2. customwas purified by PCTLC (silica gel GF rotor; 95:5 CHCl3:2M NH3 in MeOH)

Sources & evidence

ORD record
ord-fc91c8e1b6fb4fd3aca505282b20ba2b
Source dataset
uspto-grants-2007_06
Patent number
US07230011B2

Reaction notes

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