6-Chlorobenzo[b]thiophene-2-sulfonyl chloride → HCID 54352051, compound

HRID 1432997Notes

Reaction equation

HRID 1432997 reaction equation
[CH3:1][N:2]([C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1)[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][NH:8][CH2:7][C:6]1=[O:11].[Cl:18][C:19]1[CH:20]=[CH:21][C:22]2[CH:26]=[C:25]([S:27](Cl)(=[O:29])=[O:28])[S:24][C:23]=2[CH:31]=1>>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]2[CH:26]=[C:25]([S:27]([N:8]3[CH2:9][CH2:10][N:5]([CH2:4][CH2:3][N:2]([CH3:1])[C:12]4[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=4)[C:6](=[O:11])[CH2:7]3)(=[O:29])=[O:28])[S:24][C:23]=2[CH:31]=1

Participants

3

Reactant 2

HCID 151586416-Chlorobenzo[b]thiophene-2-sulfonyl chlorideHCID 54375450HCID 54375450, compound

Product 1

HCID 54352051HCID 54352051, compound

Procedure

A portion (˜50%) of the crude 1-[2-{(Methyl)-(pyridin-4-yl)-amino}-ethyl]-piperazin-2-one, EXAMPLE 93 is reacted with 6-chloro-benzo[b]thiophene-2-sulfonyl chloride (54 mg, 0.20 mmol), EXAMPLE 1, using same procedure as described in EXAMPLE 719. The residue obtained after HPLC purification is subjected to silica gel chromatography using NH4OH/MeOH/CH2Cl2 (1:4:95) as eluant to give title compound (30 mg, 0.064 mmol) as a white solid. MS m/z 465, 457 (M+1); 1H NMR (CDCl3, 300 MHz) δ8.15 (d, 2H), 7.88 (s, 1H), 7.85 (d, 1H), 7.79 (s, 1H), 7.47 (d, 1H), 6.47 (d. 2H), 3.80 (s, 2H), 3.50 (m, 4H), 3.43 (d, 2H), 3.30 (d, 2H), 2.98 (s, 3H).

Workup

  1. customThe residue obtained
  2. customafter HPLC purification

Sources & evidence

ORD record
ord-903b606e47a84526b37e2df64fb6bba8
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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