Triethylamine → HCID 69270826, compound

HRID 751580Notes

Reaction equation

HRID 751580 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:29]=[C:28]([CH:30]2[CH2:32][CH2:31]2)[NH:27][N:26]=1.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:40])=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:29]=[C:28]([CH:30]5[CH2:32][CH2:31]5)[NH:27][N:26]=4)=[O:40])[C@H:7]3[C:6]=2[C:5]([F:16])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 27580143-cyclopropyl-1H-pyrazol-5-amineHCID 21304923(1S,1aR,7bS)-4,7-difluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-1-carboxylic acid

Product 1

HCID 69270826HCID 69270826, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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), 3-amino-5-cyclopropyl-1H-pyrazole (30 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 two compounds were separated by column chromatography on silica (50 g, ethylacetate/hexane 1:3) to give 3 mg of the title product. The structure assignment was proved by 13C, gHMBC, gHMQC and NOESY NMR experiments.

Workup

  1. temperatureThe reaction mixture was then heated
  2. concentrationThe reaction mixture was concentrated by rotary evaporation and two compounds
  3. customwere separated by column chromatography on silica (50 g, ethylacetate/hexane 1:3)

Sources & evidence

ORD record
ord-9cc00014978546bfbfeb6bd24b1d9092
Source dataset
uspto-grants-2008_07
Patent number
US07405310B2

Reaction notes

Loading…