Chloroacetone → HCID 11271784, compound

HRID 1668690Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[N:9]=[CH:8][N:7]=[C:6]2[O:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[NH:28][C:27]([CH3:32])=[CH:26]2.Cl[CH2:34][C:35](=[O:37])[CH3:36].C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[C:35]([CH2:36][N:19]1[CH2:20][CH2:21][N:16]([CH2:15][CH2:14][O:13][C:12]2[CH:11]=[C:10]3[C:5]([C:6]([O:22][C:23]4[CH:24]=[C:25]5[C:29](=[CH:30][CH:31]=4)[NH:28][C:27]([CH3:32])=[CH:26]5)=[N:7][CH:8]=[N:9]3)=[CH:4][C:3]=2[O:2][CH3:1])[CH2:17][CH2:18]1)(=[O:37])[CH3:34]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]-7-[2-(piperazin-1-yl)ethoxy]quinazoline (0.15 g), chloroacetone (0.036 ml), potassium carbonate (0.05 g) and DMA (1.3 ml) was stirred and heated to 70° C. for 1.5 hours. The mixture was cooled to ambient temperature, the precipitate was filtered off and the residue was purified by preparative LCMS (Hypersil C18-β-Basic column using a solvent gradient consisting of acetonitrile and water buffered with a 5% ammonium carbonate solution (100 g/L, pH 8.9). Evaporation of the solvents gave 7-{2-[4-(acetylmethyl)piperazin-1-yl]ethoxy}-6-methoxy-4-[(2-methyl-1H-indol-5-yl)oxy]quinazoline as a pale yellow solid (0.10 g), which was dried under vacuum.

Workup

temperatureThe mixture was cooled to ambient temperature
filtrationthe precipitate was filtered off
customthe residue was purified by preparative LCMS (Hypersil C18-β-Basic column
customEvaporation of the solvents

Sources & evidence

ORD record: ord-e7cde803c5cc42ac8924ce2962dc6656
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989460B2

Reaction notes

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