Water → HCID 69136071, compound

HRID 969492Notes

Reaction equation

[CH3:1][C:2]1[N:6]([CH3:7])[C:5]2[CH:8]=[C:9]([C:22]([OH:24])=O)[C:10]3[CH2:11][CH2:12][CH:13]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[O:14][C:15]=3[C:4]=2[N:3]=1.F[B-](F)(F)F.[N:30]1(OC(N(C)C)=[N+](C)C)[C:34]2C=CC=[CH:38][C:33]=2N=N1.N1CCC1.O>ClCCl>[N:30]1([C:22]([C:9]2[C:10]3[CH2:11][CH2:12][CH:13]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[O:14][C:15]=3[C:4]3[N:3]=[C:2]([CH3:1])[N:6]([CH3:7])[C:5]=3[CH:8]=2)=[O:24])[CH2:38][CH2:33][CH2:34]1

Participants

Conditions

Temperature: 40 °C

Procedure

To a suspension of 0.31 g (0.96 mmol) 2,3-dimethyl-8-phenyl-3,6,7,8-tetrahydro-chromeno[7,8-d]imidazole-5-carboxylic acid in dichloromethane (10 ml) were added 0.34 g (1.4 mmol) O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU) and the suspension was heated at 40° C. for 4 h. 102 mg (1.0 mmol) Azetidine were added and the mixture was stirred for 3 h. The reaction mixture was poured into water and the extracted with dichloromethane. The organic layers were dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel (toluene/dioxane=1:5) and crystallized with diisopropyl ether to afford 212 mg (61%) of the title compound as a white solid. m.p. 246°-248° C.

Workup

extractionthe extracted with dichloromethane
dry with materialThe organic layers were dried over magnesium sulphate
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography on silica gel (toluene/dioxane=1:5)
customcrystallized with diisopropyl ether

Sources & evidence

ORD record: ord-ff74a5d40ead43ed9da7acc453153a8e
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07307084B2

Reaction notes

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