Triethylamine → [1-(3-Benzyloxy-1-cyclopropyl-6-fluoro-2,4-dioxo-1,2,3,4-tetrahydro-quinazolin-7-yl)-pyrrolidin-3-yl-methyl]-carbamic acid tert-butyl ester

HRID 2416848Notes

Reaction equation

[CH2:1]([O:8][N:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][C:14](Cl)=[C:15]([F:20])[CH:16]=2)[N:11]([CH:22]2[CH2:24][CH2:23]2)[C:10]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]([O:30][C:31](=[O:39])[N:32](C1CCNC1)[CH3:33])([CH3:29])([CH3:28])[CH3:27].C([N:42]([CH2:45][CH3:46])[CH2:43][CH3:44])C>CN(C=O)C.O>[C:26]([O:30][C:31](=[O:39])[NH:32][CH2:33][CH:46]1[CH2:44][CH2:43][N:42]([C:14]2[CH:13]=[C:12]3[C:17]([C:18](=[O:19])[N:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[C:10](=[O:25])[N:11]3[CH:22]3[CH2:24][CH2:23]3)=[CH:16][C:15]=2[F:20])[CH2:45]1)([CH3:29])([CH3:28])[CH3:27]

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 3-benzyloxy-7-chloro-1-cyclopropyl-6-fluoro-1H-quinazoline-2,4-dione (Example E-3, 0.162 g, 0.44 mmol) in DMF (3.0 mL) was reacted with pyrrolidin-3-yl-methyl-carbamic acid tert-butyl ester (0.40 g, 2.0 mmol) and triethylamine (0.63 mL, 4.5 mmol) then heated to 70° C. for 2 days. The mixture was then cooled, diluted with H2O, and extracted with ethyl acetate. The organic layers were combined, dried with sodium sulfate, and concentrated. The residue was then purified by column chromatography (silica gel, 1:1 hexanes/ethyl acetate) to provide 0.127 g of the title compound as a solid.

Workup

temperatureThe mixture was then cooled
extractionextracted with ethyl acetate
dry with materialdried with sodium sulfate
concentrationconcentrated
customThe residue was then purified by column chromatography (silica gel, 1:1 hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-af14b42b39e8432fb74783d33c2283ef
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06825199B2

Reaction notes

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