Pyridine → HCID 4709, compound

HRID 217965Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH2:19])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[C:26](Cl)(=[O:29])[CH2:27][CH3:28]>CN(C1C=CN=CC=1)C.C1COCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:19][C:26](=[O:29])[CH2:27][CH3:28])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 5 °C

Procedure

N4-(3-bromophenyl)quinazoline-4,6-diamine (100 mg, 0.32 mmol), pyridine (0.3 mL), and DMAP (20 mg) were dissolved in 10 mL of anhydrous THF. The solution was cooled to 5° C. Propionyl chloride (33 mg, 0.35 mmol) was added to the reaction flask dropwise. Ice bath removed was removed, and the reaction mixture was stirred at room temperature and filtered. The filtrate was dried in vacuo to give a yellow solid. The yellow solid was dissolved in ethyl acetate, washed once with saturated Na2CO3, then with 10% acetic acid, and then with brine. The organic phase was dried, filtered, and stripped of solvent in vacuo to give a crude product which was purified by TLC to give the title compound as a whitish product.

Workup

customIce bath removed
customwas removed
filtrationfiltered
customThe filtrate was dried in vacuo
customto give a yellow solid
washwashed once with saturated Na2CO3
customThe organic phase was dried
filtrationfiltered
customto give a crude product which
customwas purified by TLC

Sources & evidence

ORD record: ord-49b3dafba67b4c26aaa73221b4b55c21
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08198301B2

Reaction notes

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