4-Methylbenzoyl Chloride → HCID 25005209, compound

HRID 1015399Notes

Reaction equation

HRID 1015399 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([CH3:28])[CH:24]=[CH:23][C:22]([C:25](Cl)=[O:26])=[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:25]([C:22]3[CH:23]=[CH:24][C:19]([CH3:28])=[CH:20][CH:21]=3)=[O:26])[CH2:3][CH2:2]2)[N:12]=1

Participants

3

Reactant 2

HCID 134054-Methylbenzoyl ChlorideHCID 180713185-Piperazin-1-yl-quinazoline-2,4-diamine

Product 1

HCID 25005209HCID 25005209, compoundYield 41%

Procedure

Title compound was prepared via Resin Method using 5-piperazin-1-yl-quinazoline-2,4-diamine (50 mg; 0.2 mmol) and p-toluoyl chloride (63.4 mg; 0.41 mmol) to obtain 29.5 mg. (41% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.78 (s, 1H), 7.37 (m, 2H), 7.26 (m, 3H), 7.14 (br s, 1H), 6.98 (d, J=6.4 Hz, 1H), 6.86 (d, J=5.6 Hz, 1H), 5.92 (br s, 2H), 4.58 (br s, 1H), 4.35 (br s, 1H), 3.66 (br s, 1H), 3.44 (m, 1H), 3.11 (m, 3H), 2.77 (m, 2H), 2.35 (s, 3H). ESIMS+363.8 m/z

Workup

  1. customto obtain 29.5 mg

Sources & evidence

ORD record
ord-12b73b7965c840328a505d8f142a3edc
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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