Bis-(1H-imidazol-2-YL)-methanone → 3,4-dihydro-6-hydroxy-3-(1-phenylmethyl-4-piperidinyl)-2(1H)-quinazolinone

HRID 1353602Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH2:9][NH:10][CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][CH2:12]1.[C:24](C1NC=CN=1)(C1NC=CN=1)=[O:25]>O1CCCC1>[CH2:17]([N:14]1[CH2:13][CH2:12][CH:11]([N:10]2[CH2:9][C:3]3[C:2](=[CH:7][CH:6]=[C:5]([OH:8])[CH:4]=3)[NH:1][C:24]2=[O:25])[CH2:16][CH2:15]1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A stirred solution of 4-amino-3-[(1-benzyl-piperidin-4-yl-amino)-methyl]phenol (0.16 g, 0.51 mmol) in tetrahydrofuran (3 mL) at 0° C. was treated with carbonyl diimidazole (52 mg, 0.51 mmol). The reaction was stirred for 30 min at 0° C. and at reflux for 1 h. After cooling to room temperature, the solvent was evaporated and the residue purified by column to afford 100 mg (57%) of the desired product. LC/MS: tR=1.09 min, 338.28 (MH)+.

Workup

temperatureat reflux for 1 h
temperatureAfter cooling to room temperature
customthe solvent was evaporated
customthe residue purified by column

Sources & evidence

ORD record: ord-635a5f84e0c9428a8182fdb3285efb16
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07220862B2

Reaction notes

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