2-Naphthalenesulfonyl chloride → HCID 25005931, compound

HRID 1015411Notes

Reaction equation

HRID 1015411 reaction equation
[N:1]1([C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[C:9]([NH2:18])=[N:10][C:11]([NH2:17])=[N:12]3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][C:20]=1[S:29](Cl)(=[O:31])=[O:30]>>[CH:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][C:20]=1[S:29]([N:4]1[CH2:5][CH2:6][N:1]([C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[C:9]([NH2:18])=[N:10][C:11]([NH2:17])=[N:12]3)[CH2:2][CH2:3]1)(=[O:30])=[O:31]

Participants

3

Reactant 2

HCID 71252-Naphthalenesulfonyl chlorideHCID 180713185-Piperazin-1-yl-quinazoline-2,4-diamine

Product 1

HCID 25005931HCID 25005931, compoundYield 58%

Procedure

Title compound was prepared via Resin Method using 5-piperazin-1-yl-quinazoline-2,4-diamine (50 mg; 0.2 mmol) and 2-naphthalene-sulfonyl chloride (79.8 mg; 0.41 mmol) to obtain 50.0 mg. (58% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.52 (s, 1H), 8.31 (br s, 1H), 8.23 (m, 2H), 8.13 (m, 1H), 7.84 (m, 1H), 7.77 (m, 2H), 7.37 (m, 1H), 6.96 (d, J=8.0 Hz, 1H), 6.83 (m, 2H), 5.90 (br s, 2H), 3.82 (br d, J=11.2 Hz, 2H), 3.11 (br d, J=12.0 Hz, 2H), 2.87 (m, 2H), 2.64 (m, 2H). ESIMS+436.0 m/z

Workup

  1. customto obtain 50.0 mg

Sources & evidence

ORD record
ord-d91275574ccb42a0bce309f1bfae0f62
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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