2-Chlorobenzenesulfonyl chloride → 5-[4-(2-Chlorobenzenesulfonyl)piperidin-4-ylmethoxy]quinazoline-2,4-diamine

HRID 1015353Notes

Reaction equation

HRID 1015353 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:27]=[CH:26][CH:25]=[CH:24][C:23]=1[S:28](Cl)(=[O:30])=[O:29]>>[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[S:28]([C:4]1([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)[CH2:5][CH2:6][NH:1][CH2:2][CH2:3]1)(=[O:30])=[O:29]

Participants

3

Reactant 2

HCID 761872-Chlorobenzenesulfonyl chlorideHCID 575765655-(Piperidin-4-ylmethoxy)quinazoline-2,4-diamine

Product 1

HCID 250031115-[4-(2-Chlorobenzenesulfonyl)piperidin-4-ylmethoxy]quinazoline-2,4-diamineYield 99%

Procedure

The sulfonamide was obtained by reacting 5-(piperidin-4-ylmethoxy)quinazoline-2,4-diamine (50 mg; 0.18 mmol) and 2-chlorobenzenesulfonyl chloride (78 mg; 0.37 mmol) via Method AA to yield 80 mg. (99% yield). 1HNMR (400 MHz, DMSO-d6) δ 7.97 (dd, J=7.6, 1.2 Hz, 1H), 7.69 (m, 2H), 7.57 (m, 1H), 7.33 (t, J=8.4 Hz, 1H), 7.12 (br s, 2H), 6.76 (d, J=8.0 Hz, 1H), 6.52 (d, J=7.6 Hz, 1H), 5.93 (br s, 2H), 3.99 (d, J=6.0 Hz, 2H), 3.77 (br d, J=12.0 Hz, 2H), 2.75 (t, J=10.8 Hz, 2H), 2.06 (s, 1H), 1.84 (d, J=10.8 Hz, 2H), 1.31 (m, 2H). MS m/z (ESI) 448 (M+H)+.

Workup

  1. customto yield 80 mg

Sources & evidence

ORD record
ord-16cce8504bc3408a9478816eb3538f4f
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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