HCID 54238815, compound → HCID 54033765, compound

HRID 1432998Notes

Reaction equation

HRID 1432998 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][NH:14][CH2:13][C:12]1=[O:17].[Cl:18][C:19]1[S:23][C:22]([CH:24]=[CH:25][S:26](Cl)(=[O:28])=[O:27])=[CH:21][CH:20]=1>>[Cl:18][C:19]1[S:23][C:22]([CH:24]=[CH:25][S:26]([N:14]2[CH2:15][CH2:16][N:11]([CH2:10][CH2:9][NH:8][C:7]3[CH:6]=[CH:5][N:4]=[CH:3][C:2]=3[CH3:1])[C:12](=[O:17])[CH2:13]2)(=[O:28])=[O:27])=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 54238815HCID 54238815, compoundHCID 544630642-(5-Chlorothiophen-2-yl)ethenesulfonyl chloride

Product 1

HCID 54033765HCID 54033765, compoundYield 32.5%

Procedure

1-[2-(3-Methylpyridin-4-yl-amino)-ethyl]-piperazin-2-one (38 mg, 0.16 mmol), EXAMPLE 94, is reacted with 2-(5-chloro-thiophen-2-yl)-ethenesulfonyl chloride (40 mg, 0.16 mmol), EXAMPLE 3, using the same procedure as described in EXAMPLE 719. Reverse phase HPLC purification gives the title compound (29 mg, 0.052 mmol) as a white solid. MS m/z 441, 443 (M+H); 1H NMR (CD3OD, 300 MHz) δ8.08 (d, 1H), 7.98 (s, 1H), 7.56 (d, 1H), 7.30 (d, 1H), 7.02 (s, 1H), 7.00 (d. 1H), 6.78 (d, 1H), 3.87 (s, 2H), 3.70-3.50 (m, 8H), 2.15 (s, 3H).

Workup

  1. customReverse phase HPLC purification

Sources & evidence

ORD record
ord-704cc992f6a9466db1fb92a166c94e2d
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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