1-Naphthalenecarbonyl chloride → HCID 25005571, compound

HRID 1015407Notes

Reaction equation

HRID 1015407 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.[C:19]1([C:29](Cl)=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1>>[NH2:17][C:11]1[N:10]=[C:9]([NH2:18])[C:8]2[C:13](=[CH:14][CH:15]=[CH:16][C:7]=2[N:1]2[CH2:6][CH2:5][N:4]([C:29]([C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH:22]=[CH:21][CH:20]=3)=[O:30])[CH2:3][CH2:2]2)[N:12]=1

Participants

3

Reactant 2

HCID 701461-Naphthalenecarbonyl chlorideHCID 180713185-Piperazin-1-yl-quinazoline-2,4-diamine

Product 1

HCID 25005571HCID 25005571, compoundYield 28%

Procedure

Title compound was prepared via Resin Method using 5-piperazin-1-yl-quinazoline-2,4-diamine (50 mg; 0.2 mmol) and 1-Naphthoyl chloride (78.2 mg; 0.41 mmol) to obtain 22.1 mg. (28% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.86 (s, 1H), 8.0 (d, J=7.6 Hz, 2H), 7.75 (br d, 1H), 7.59 (m, 3H), 7.45 (m, 2H), 7.30 (br s, 1H), 6.98 (d, J=8.0 Hz, 1H), 6.89 (dd, J=17.6, 7.6 Hz, 1H), 6.11 (br s, 2H), 4.78 (br t, 1H), 3.42 (m, 2H), 3.24 (m, 3H), 2.89 (m, 2H). ESIMS+400.0 m/z

Workup

  1. customto obtain 22.1 mg

Sources & evidence

ORD record
ord-90280db9796f4fb792160f0f2247a9e2
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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