2,4-Difluorobenzenesulfonyl Chloride → HCID 25003476, compound

HRID 1015355Notes

Reaction equation

HRID 1015355 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.[F:21][C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=1[S:29](Cl)(=[O:31])=[O:30]>>[F:21][C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=1[S:29]([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:31])=[O:30]

Participants

3

Reactant 2

HCID 27342732,4-Difluorobenzenesulfonyl ChlorideHCID 575765655-(Piperidin-4-ylmethoxy)quinazoline-2,4-diamine

Product 1

HCID 25003476HCID 25003476, compoundYield 99%

Procedure

The sulfonamide was obtained by reacting 5-(piperidin-4-ylmethoxy)quinazoline-2,4-diamine (50 mg; 0.18 mmol) and 2,4-difluorobenzenesulfonyl chloride (79 mg; 0.37 mmol) via Method AA to yield 80 mg. (99% yield). 1HNMR (400 MHz, DMSO-d6) δ 7.86 (m, 1H), 7.61 (m, 1H), 7.33 (m, 2H), 7.12 (br s, 2H), 6.75 (d, J=8.0 Hz, 1H), 6.51 (d, J=7.6 Hz, 1H), 5.93 (br s, 2H), 3.97 (d, J=6.0 Hz, 2H), 3.71 (br d, J=12.0 Hz, 2H), 2.56 (t, J=12 Hz, 2H), 2.0 (s, 1H), 1.85 (d, J=10.4 Hz, 2H), 1.34 (m, 2H). MS m/z (ESI) 451 (M+H)+.

Workup

  1. customto yield 80 mg

Sources & evidence

ORD record
ord-d7b0450b7fcf4aff98c69bfbd1f3b0a8
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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