4-Fluorobenzoyl chloride → HCID 25005568, compound

HRID 1015405Notes

Reaction equation

HRID 1015405 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.[F:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=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:24]([C:23]3[CH:27]=[CH:28][C:20]([F:19])=[CH:21][CH:22]=3)=[O:25])[CH2:3][CH2:2]2)[N:12]=1

Participants

3

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 180713185-Piperazin-1-yl-quinazoline-2,4-diamine

Product 1

HCID 25005568HCID 25005568, compoundYield 36%

Procedure

Title compound was prepared via Resin Method using 5-piperazin-1-yl-quinazoline-2,4-diamine (50 mg; 0.2 mmol) and 4-fluorobenzoyl chloride (65 mg; 0.41 mmol) to obtain 26 mg. (36% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.78 (s, 1H), 7.54 (m, 2H), 7.39 (t, J=8.0 Hz, 1H), 7.30 (m, 2H), 7.16 (br s, 1H), 6.98 (d, J=8.0 Hz, 1H), 6.85 (d, J=8.0 Hz, 1H), 5.93 (br s, 2H), 4.55 (br s, 1H), 3.67 (br s, 1H), 3.37 (m, 2H), 3.08 (m, 2H), 2.77 (m, 2H). ESIMS+367.5 m/z

Workup

  1. customto obtain 26 mg

Sources & evidence

ORD record
ord-eb504c8d817a4ee5a6d692eabd99e352
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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