1-Chloro-4-(chloromethyl)benzene → 5-[4-(4-Chloro-benzyl)-piperazin-1-yl]-quinazoline-2,4-diamine

HRID 1015387Notes

Reaction equation

HRID 1015387 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:27]=[CH:26][C:23]([CH2:24]Cl)=[CH:22][CH:21]=1>>[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][N:4]2[CH2:5][CH2:6][N:1]([C:7]3[CH:16]=[CH:15][CH:14]=[C:13]4[C:8]=3[C:9]([NH2:18])=[N:10][C:11]([NH2:17])=[N:12]4)[CH2:2][CH2:3]2)=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 180713185-Piperazin-1-yl-quinazoline-2,4-diamine

Product 1

HCID 250045305-[4-(4-Chloro-benzyl)-piperazin-1-yl]-quinazoline-2,4-diamineYield 67%

Procedure

Title compound was prepared via Resin Method using 5-piperazin-1-yl-quinazoline-2,4-diamine (50 mg; 0.2 mmol) and 4-Chlorobenzyl Chloride (59.6 mg; 0.37 mmol) to obtain 49.5 mg. (67% yield). 1H NMR (400 MHz, DMSO-d6) δ 12.8 (s, 1H), 9.94 (s, 1H), 8.88 (s, 1H), 7.69 (m, 2H), 7.38 (m, 4H), 7.25 (d, J=8.0 Hz, 1H), 7.21 (d, J=8.4 Hz, 1H), 3.57 (s, 2H), 3.03 (br d, J=10.8 Hz, 3H), 2.91 (m, 3H), 2.29 (m, 2H). ESIMS+369.2 m/z

Workup

  1. customto obtain 49.5 mg

Sources & evidence

ORD record
ord-2728b7c697b7494d81a2837e8410c9be
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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