Triethylamine → HCID 9867190, compound

HRID 2110951Notes

Reaction equation

HRID 2110951 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.[F:24][C:25]1[CH:26]=[C:27]([CH:36]=[CH:37][CH:38]=1)[O:28][C:29]1[CH:30]=[CH:31][C:32]([NH2:35])=[N:33][CH:34]=1.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:46])=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:35][C:32]4[CH:31]=[CH:30][C:29]([O:28][C:27]5[CH:36]=[CH:37][CH:38]=[C:25]([F:24])[CH:26]=5)=[CH:34][N:33]=4)=[O:46])[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 28412179HCID 28412179, compound

Product 1

HCID 9867190HCID 9867190, 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, ˜95% ee) was mixed with toluene (1,5 ml), triethylamine (1.1 eq), 5-(3-fluorophenoxy)-2-aminopyridine (1.1 eq), DPPA (1.1 eq) and bubbled with argon for about 5 min. 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 mtary evaporation and purified by column chromatography on silica (30 g, ethylacetate/hexane 1:1). Desired product was obtained as beige-white powder (60 mg, yield 64%).

Workup

  1. custombubbled with argon for about 5 min
  2. temperatureThe reaction mixture was then heated
  3. concentrationThe reaction mixture was concentrated by mtary evaporation
  4. custompurified by column chromatography on silica (30 g, ethylacetate/hexane 1:1)

Sources & evidence

ORD record
ord-2d55a1da4d0142a08b4593f2b5702a21
Source dataset
uspto-grants-2009_04
Patent number
US07517992B2

Reaction notes

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