3-Chlorobenzenesulphonyl chloride → HCID 25002764, compound

HRID 1015352Notes

Reaction equation

HRID 1015352 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.[Cl:21][C:22]1[CH:23]=[C:24]([S:28](Cl)(=[O:30])=[O:29])[CH:25]=[CH:26][CH:27]=1>>[Cl:21][C:22]1[CH:23]=[C:24]([S:28]([C:4]2([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)[CH2:5][CH2:6][NH:1][CH2:2][CH2:3]2)(=[O:30])=[O:29])[CH:25]=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 179093-Chlorobenzenesulphonyl chlorideHCID 575765655-(Piperidin-4-ylmethoxy)quinazoline-2,4-diamine

Product 1

HCID 25002764HCID 25002764, compoundYield 99%

Procedure

The sulfonamide was obtained by reacting 5-(piperidin-4-ylmethoxy)quinazoline-2,4-diamine (50 mg; 0.18 mmol) and 3-chlorobenzenesulfonyl chloride (78 mg; 0.37 mmol) via Method AA to yield 80 mg. (99% yield). 1HNMR (400 MHz, DMSO-d6) δ 7.82 (m, 1H), 7.72 (m, 3H), 7.32 (t, J=8.4 Hz, 1H), 7.11 (br s, 2H), 6.75 (d, J=8.0 Hz, 1H), 6.50 (d, J=7.6 Hz, 1H), 5.93 (br s, 2H), 3.96 (d, J=6.4 Hz, 2H), 3.72 (br d, J=11.6 Hz, 2H), 2.32 (t, J=12 Hz, 2H), 1.84 (m, 3H), 1.36 (m, 2H). MS m/z (ESI) 448 (M+H)+.

Workup

  1. customto yield 80 mg

Sources & evidence

ORD record
ord-421bdf31da8f4470bc3540cf2cab8c98
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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