HCID 68689700, compound → HCID 68685883, compound

HRID 1172788Notes

Reaction equation

HRID 1172788 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[CH:11]=[C:10]([CH2:12][C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[C:15]([F:21])[CH:14]=2)[N:9]2[CH:22]=[CH:23][CH:24]=[C:8]2[C:7]1=[O:25]>C(Cl)Cl.C(O)(C(F)(F)F)=O.C1(C)C=CC=CC=1>[F:21][C:15]1[CH:14]=[C:13]([CH2:12][C:10]2[N:9]3[CH:22]=[CH:23][CH:24]=[C:8]3[C:7](=[O:25])[NH:6][CH:11]=2)[CH:20]=[CH:19][C:16]=1[C:17]#[N:18]

Participants

5

Reactant 1

HCID 68689700HCID 68689700, compound

Product 1

HCID 68685883HCID 68685883, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
120 °C

Procedure

A solution of A3 (1 eq) in a mixture of DCM and TFA (2:1) was heated in a microwave oven at 120° C. for 10 min. The reaction mixture was diluted with DCM and toluene and concentrated under reduced pressure. The resulting crude was diluted with DCM and washed with sat. aq. NaHCO3 solution, dried (Na2SO4) and concentrated under reduced pressure. The resulting crude was purified by Biotage system eluting with EtOAc/petrol ether to obtain the desired compound. MS (ES) C15H10FN3O requires: 267, found: 268 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ: 10.51 (1H, d, J=5.3 Hz), 7.97 (1H, dd, J=6.3, 2.0 Hz), 7.79-7.72 (1H, m), 7.47 (1H, t, J=9.0 Hz), 7.34-7.30 (1H, m), 6.92-6.88 (1H, m), 6.54-6.49 (2H, m), 4.08 (2H, s).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe resulting crude was diluted with DCM
  3. washwashed with sat. aq. NaHCO3 solution
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting crude was purified by Biotage system
  7. washeluting with EtOAc/petrol ether

Sources & evidence

ORD record
ord-dbd1cb2cfb304d67a2e6e9598bd2d69d
Source dataset
uspto-grants-2010_11
Patent number
US07834015B2

Reaction notes

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