6-Chlorobenzo[b]thiophene-2-sulfonyl chloride → HCID 53884463, compound

HRID 1432999Notes

Reaction equation

HRID 1432999 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][NH:14][CH2:13][C:12]2=[O:17])=[CH:4][N:3]=1.[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:14]3[CH2:15][CH2:16][N:11]([CH2:10][CH2:9][NH:8][C:5]4[CH:6]=[CH:7][N:2]=[N:3][CH:4]=4)[C:12](=[O:17])[CH2:13]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 690261851-[2-(Pyridazin-4-ylamino)-ethyl]-piperazin-2-one hydrochloride

Product 1

HCID 53884463HCID 53884463, compoundYield 50%

Procedure

1-[2-(Pyridazin-4-ylamino)-ethyl]-piperazin-2-one hydrochloride (0.5 g, 1.7 mmol), EXAMPLE 95, is reacted with 6-chloro-benzo[b]thiophene-2-sulfonyl chloride (0.40 g, 1.5 mmol), EXAMPLE 1, using essentially the same procedure as described in EXAMPLE 719. Reverse phase HPLC purification gives the title compound (0.34 g, 0.75 mmol) as a white solid. MS m/z (M+H=452); 1H NMR (CD3OD, 300 MHz) δ8.6 (d, 1H), 8.4 (d, 1H), 8.05 (s, 1H), 8.05 (s, 1H), 7.9 (d, 1H), 7.5 (d, 1H), 7.2 (d, 1H), 3.8 (s, 2H), 3.4-3.7 (m, 8H).

Workup

  1. customReverse phase HPLC purification

Sources & evidence

ORD record
ord-5f66cb21df6d4b5b84d4f28ed61387b6
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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