3,4-Difluorobenzene-1-sulfonyl chloride → HCID 25003477, compound

HRID 1015356Notes

Reaction equation

HRID 1015356 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:23]=[C:24]([S:29](Cl)(=[O:31])=[O:30])[CH:25]=[CH:26][C:27]=1[F:28]>>[F:21][C:22]1[CH:23]=[C:24]([S:29]([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:31])[CH:25]=[CH:26][C:27]=1[F:28]

Participants

3

Reactant 2

HCID 27369133,4-Difluorobenzene-1-sulfonyl chlorideHCID 575765655-(Piperidin-4-ylmethoxy)quinazoline-2,4-diamine

Product 1

HCID 25003477HCID 25003477, compoundYield 99%

Procedure

The sulfonamide was obtained by reacting 5-(piperidin-4-ylmethoxy)quinazoline-2,4-diamine (50 mg; 0.18 mmol) and 3,4-difluorobenzenesulfonyl chloride (79 mg; 0.37 mmol) via Method AA to yield 80 mg. (99% yield). 1HNMR (400 MHz, DMSO-d6) δ 7.88 (m, 1H), 7.73 (m, 1H), 7.65 (m, 1H), 7.33 (t, J=8.0 Hz, 1H), 7.11 (br s, 2H), 6.75 (dd, J=8.0, 0.4 Hz, 1H), 6.50 (d, J=7.6 Hz, 1H), 5.93 (br s, 2H), 3.97 (d, J=6.0 Hz, 2H), 3.69 (br d, J=11.6 Hz, 2H), 2.34 (m, 2H), 1.87 (m, 3H), 1.36 (m, 2H). MS m/z (ESI) 450 (M+H)+.

Workup

  1. customto yield 80 mg

Sources & evidence

ORD record
ord-a69482eb481847d08bdb2a3f1004efad
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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