Hydrochloric Acid → HCID 21717207, compound

HRID 1386303Notes

Reaction equation

[ClH:1].C(OC(OCC)[N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]([C:15]2[C:24]3[C:19](=[CH:20][C:21]([O:27][CH2:28][CH2:29][CH2:30][N:31]4[CH2:35][CH2:34][CH2:33][CH2:32]4)=[C:22]([O:25][CH3:26])[CH:23]=3)[N:18]=[CH:17][N:16]=2)[C:7]1=[O:36])C>C(O)C>[ClH:1].[CH3:26][O:25][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][C:21]=1[O:27][CH2:28][CH2:29][CH2:30][N:31]1[CH2:32][CH2:33][CH2:34][CH2:35]1)[N:18]=[CH:17][N:16]=[C:15]2[CH:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:6][C:7]1=[O:36]

Participants

Conditions

Temperature: 80 °C

Procedure

2M Hydrochloric acid (1.5 ml, 3 mmol) was added to a solution of 4-(1-diethoxymethyloxindol-3-yl)-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline (151 mg, 0.29 mmol), (prepared as described in Example 24), in ethanol (15 ml) at 80° C. and the mixture was stirred at 80° C. for 1.5 hours. The reaction mixture was allowed to cool, the solvent was removed by evaporation and the residue was purified by reverse phase C18 chromatography eluting with a gradient of acetonitrile in water (0-40%). The acetonitrile was removed by evaporation from the fractions containing product and concentrated hydrochloric acid (0.1 ml) was added to the aqueous phase. The solution was freeze dried to give 6-methoxy4-(oxindol-3-yl)-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline hydrochloride (150 mg, 100%).

Workup

temperatureto cool
customthe solvent was removed by evaporation
customthe residue was purified by reverse phase C18 chromatography
washeluting with a gradient of acetonitrile in water (0-40%)
customThe acetonitrile was removed by evaporation from the fractions
additioncontaining product and concentrated hydrochloric acid (0.1 ml)
additionwas added to the aqueous phase
customdried

Sources & evidence

ORD record: ord-26de0844faaa45ba81a767445cd46110
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06265411B1

Reaction notes

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