Benzoyl chloride, 3,4-dichloro- → [4-(2,4-Diamino-quinazolin-5-yl)-piperazin-1-yl]-(3,4-dichloro-phenyl)-methanone

HRID 1015403Notes

Reaction equation

HRID 1015403 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.[Cl:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][C:28]=1[Cl:29])[C:23](Cl)=[O:24]>>[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:23]([C:22]3[CH:26]=[CH:27][C:28]([Cl:29])=[C:20]([Cl:19])[CH:21]=3)=[O:24])[CH2:3][CH2:2]2)[N:12]=1

Participants

3

Reactant 2

HCID 76403Benzoyl chloride, 3,4-dichloro-HCID 180713185-Piperazin-1-yl-quinazoline-2,4-diamine

Product 1

HCID 25005214[4-(2,4-Diamino-quinazolin-5-yl)-piperazin-1-yl]-(3,4-dichloro-phenyl)-methanoneYield 63%

Procedure

Title compound was prepared via Resin Method using 5-piperazin-1-yl-quinazoline-2,4-diamine (50 mg; 0.2 mmol) and 3,4-Dichlorobenzoyl chloride (85.9 mg; 0.41 mmol) to obtain 52.5 mg. (63% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.77 (br s, 1H), 7.75 (m, 2H), 7.47 (m, 1H), 7.4 (t, J=8.0 Hz, 1H), 7.18 (br s, 1H), 6.98 (dd, J=8.4, 0.8 Hz, 1H), 6.85 (dd, J=7.6, 0.8 Hz, 1H), 5.93 (s, 2H), 4.55 (br s, 1H), 3.61 (br s, 1H), 3.45 (br s, 1H), 3.14 (m, 3H), 2.79 (m, 2H). ESIMS+419.3 m/z

Workup

  1. customto obtain 52.5 mg

Sources & evidence

ORD record
ord-036753adead8412f9747384931e57082
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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