Methanesulfonyl chloride → HCID 21473567, compound

HRID 2294157Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][NH:17][C:18]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:19]=2[C:20]([N:22]([CH3:24])[CH3:23])=[O:21])[CH2:10][CH2:9]1.[CH3:30][S:31]([Cl:34])(=[O:33])=[O:32]>N1C=CC=CC=1>[ClH:34].[CH3:30][S:31]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][NH:17][C:18]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:19]=2[C:20]([N:22]([CH3:24])[CH3:23])=[O:21])[CH2:10][CH2:9]1)(=[O:33])=[O:32]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2-{3-[4-(2-aminophenyl)piperazin-1-yl]propylamino}-N,N,5-trimethylbenzamide (398 mg, 1.01 mmol), prepared as in Example 36, in 10 mL of pyridine was cooled to 0° C. and methanesulfonyl chloride (0.08 mL, 1.03 mmol) was added slowly. The mixture was stirred at 0° C. for 2 hours and then evaporated to dryness. The residue was partioned between saturated sodium bicarbonate and ethyl acetate. The organic layer was separated, dried (K2CO3) and evaporated to dryness. The residue was purified on silica gel by column chromatography eluting with 5% methanol/methylene chloride to give 2-{3-[4-(2-methylsulfonylaminophenyl)-piperazin-1-yl]propylamino}-N,N,5-trimethylbenzamide hydrochloride, m.p. 207°-209° C.; Anal.: Calcd. for C24H35N5O3S.(HCl)2.(H2 O)0.5 : C, 51.89; H, 6.90; N, 12.61%; Found: C, 51.9; H, 6.74.; N, 12.56%.

Workup

customevaporated to dryness
customThe organic layer was separated
dry with materialdried (K2CO3)
customevaporated to dryness
customThe residue was purified on silica gel by column chromatography
washeluting with 5% methanol/methylene chloride

Sources & evidence

ORD record: ord-c55bca73fa514ed3985a2e8107749e8b
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05688795

Reaction notes

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