3-Methylbenzenesulphonyl chloride → HCID 25003116, compound

HRID 1015354Notes

Reaction equation

HRID 1015354 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][O:8][C:9]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:10]=2[C:11]([NH2:20])=[N:12][C:13]([NH2:19])=[N:14]3)[CH2:3][CH2:2]1.[C:21]1([CH3:31])[CH:26]=[CH:25][CH:24]=[C:23]([S:27](Cl)(=[O:29])=[O:28])[CH:22]=1>>[C:21]1([CH3:31])[CH:26]=[CH:25][CH:24]=[C:23]([S:27]([N:1]2[CH2:6][CH2:5][CH:4]([CH2:7][O:8][C:9]3[CH:18]=[CH:17][CH:16]=[C:15]4[C:10]=3[C:11]([NH2:20])=[N:12][C:13]([NH2:19])=[N:14]4)[CH2:3][CH2:2]2)(=[O:29])=[O:28])[CH:22]=1

Participants

3

Reactant 2

HCID 27345953-Methylbenzenesulphonyl chlorideHCID 575765655-(Piperidin-4-ylmethoxy)quinazoline-2,4-diamine

Product 1

HCID 25003116HCID 25003116, compoundYield 83%

Procedure

The sulfonamide was obtained by reacting 5-(piperidin-4-ylmethoxy)quinazoline-2,4-diamine (50 mg; 0.18 mmol) and m-toluenesulfonyl chloride (71 mg; 0.37 mmol) via Method AA to yield 131 mg. (83% yield). 1HNMR (400 MHz, DMSO-d6) δ 7.54 (m, 4H), 7.47 (t, J=8.4 Hz, 1H), 7.10 (br s, 2H), 6.75 (d, J=8.4 Hz, 1H), 6.49 (d, J=8.0 Hz, 1H), 5.93 (br s, 2H), 3.95 (d, J=6.0 Hz, 2H), 3.69 (br d, J=11.6 Hz, 2H), 2.42 (s, 3H), 2.23 (t, J=12.0 Hz, 2H), 1.86 (m, 3H), 1.36 (m, 2H). MS m/z (ESI) 428 (M+H)+.

Workup

  1. customto yield 131 mg

Sources & evidence

ORD record
ord-6ba4cf6e165f466eb018140d4d02dc6a
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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