Triethylamine → N-[(1S,1aR,7bR)-4,7-difluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromen-1-yl]-N'-(5-fluoro-2-pyridinyl)urea
Reaction equation
[F:1][C:2]1[C:11]2[O:10][CH2:9][C@H:8]3[C@@H:12](C(O)=O)[C@H:7]3[C:6]=2[C:5]([F:16])=[CH:4][CH:3]=1.C([N:19]([CH2:22]C)CC)C.[NH2:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][N:26]=1.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:39])=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[C:11]2[O:10][CH2:9][C@H:8]3[C@@H:12]([NH:19][C:22]([NH:24][C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][N:26]=4)=[O:39])[C@H:7]3[C:6]=2[C:5]([F:16])=[CH:4][CH:3]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
(1S,1aR,7bS)-4,7-difluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-1-carboxylic acid (50 mg, 0.22 mmol, ee ˜90%) was mixed with toluene (1 ml), triethylamine (0.034 ml, 1.1 eq), 2-amino-5-fluoropyridine (28 mg, 1.1 eq), DPPA (0.054 ml, 1.1 eq). The reaction mixture was then heated at stirring at 110° C. for 3 h. The reaction mixture was concentrated by rotary evaporation and purified by column chromatography on silica (50 g, ethylacetate/hexane 1:1) to give 30 mg of the product as white solid.
Workup
- temperatureThe reaction mixture was then heated
- concentrationThe reaction mixture was concentrated by rotary evaporation
- custompurified by column chromatography on silica (50 g, ethylacetate/hexane 1:1)
Sources & evidence
- ORD record
- ord-88b338c1d8f24e26b842e031008e859d
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07405310B2
Reaction notes
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