Triethylamine → HCID 69055100, compound

HRID 2110988Notes

Reaction equation

HRID 2110988 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[N:30]=[CH:29][C:28]([C:31]([C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)=[O:32])=[CH:27][CH:26]=1.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:47])=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:26]=[CH:27][C:28]([C:31](=[O:32])[C:33]5[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=5)=[CH:29][N:30]=4)=[O:47])[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 21304923(1S,1aR,7bS)-4,7-difluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-1-carboxylic acidHCID 22626666HCID 22626666, compound

Product 1

HCID 69055100HCID 69055100, compoundYield 39%

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 (40 mg, 0.18 mmol, ˜95% ee) was mixed with toluene (1 ml), triethylamine (1.1 eq), (6-amino-3-pyridinyl)(4-fluorophenyl)methanone (1.1 eq), DPPA (1.1 eq) and bubbled with argon. The reaction mixture was then heated at stirring at 110° C. for 3 h under in a closed vial. The reaction mixture was concentrated by rotary evaporation and purified by column chromatography on silica (30 g, ethylacetate/hexane 1:4). The last fraction collected contained desired product together with starting aminopyridine (25%, NMR data). The mixture was dissolved in methylene chloride and washed with 1N HCl, water and brine. Organic layer was dried over magnesium sulphate. Concentration gave pure product as white powder (30 mg, yield 39%).

Workup

  1. custombubbled with argon
  2. temperatureThe reaction mixture was then heated
  3. concentrationThe reaction mixture was concentrated by rotary evaporation
  4. custompurified by column chromatography on silica (30 g, ethylacetate/hexane 1:4)
  5. customThe last fraction collected
  6. dissolutionThe mixture was dissolved in methylene chloride
  7. washwashed with 1N HCl, water and brine
  8. dry with materialOrganic layer was dried over magnesium sulphate
  9. concentrationConcentration

Sources & evidence

ORD record
ord-68278d43d5a341ae89933827144928ce
Source dataset
uspto-grants-2009_04
Patent number
US07517992B2

Reaction notes

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