3-Methylbenzenesulphonyl chloride → HCID 25005930, compound

HRID 1015410Notes

Reaction equation

HRID 1015410 reaction equation
[N:1]1([C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[C:9]([NH2:18])=[N:10][C:11]([NH2:17])=[N:12]3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:19]1([CH3:29])[CH:24]=[CH:23][CH:22]=[C:21]([S:25](Cl)(=[O:27])=[O:26])[CH:20]=1>>[C:19]1([CH3:29])[CH:24]=[CH:23][CH:22]=[C:21]([S:25]([N:4]2[CH2:5][CH2:6][N:1]([C:7]3[CH:16]=[CH:15][CH:14]=[C:13]4[C:8]=3[C:9]([NH2:18])=[N:10][C:11]([NH2:17])=[N:12]4)[CH2:2][CH2:3]2)(=[O:27])=[O:26])[CH:20]=1

Participants

3

Reactant 2

HCID 27345953-Methylbenzenesulphonyl chlorideHCID 180713185-Piperazin-1-yl-quinazoline-2,4-diamine

Product 1

HCID 25005930HCID 25005930, compoundYield 41%

Procedure

Title compound was prepared via Resin Method using 5-piperazin-1-yl-quinazoline-2,4-diamine (50 mg; 0.2 mmol) and m-toluenesulfonyl chloride (78.2 mg; 0.41 mmol) to obtain 32.3 mg. (41% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.37 (s, 1H), 7.58 (m, 4H), 7.38 (t, J=8.0 Hz, 1H), 6.96 (d, J=8.0 Hz, 1H), 6.84 (d, J=7.6 Hz, 1H), 5.92 (br s, 2H), 3.74 (br d, J=11.6 Hz, 2H), 3.44 (m, 1H), 3.1 (br d, J=12 Hz, 2H), 2.85 (m, 2H), 2.53 (m, 4H). ESIMS+399.6 m/z

Workup

  1. customto obtain 32.3 mg

Sources & evidence

ORD record
ord-682cd3c2ef65423b96be54fb0e3405b7
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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