Diisopropylethylamine → HCID 59805856, compound

HRID 1429667Notes

Reaction equation

HRID 1429667 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[F:17])[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([NH:12][CH3:13])[CH2:8][CH2:7]1.Cl[C:19]1[N:20]=[N:21][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:23][CH:24]=1.C(N(C(C)C)CC)(C)C>C(O)CCC>[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[F:17])[CH2:5][N:6]1[CH2:7][CH2:8][CH:9]([N:12]([CH3:13])[C:19]2[N:20]=[N:21][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:23][CH:24]=2)[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 282425263-Chloro-6-(trifluoromethyl)pyridazineHCID 54965987HCID 54965987, compound

Product 1

HCID 59805856HCID 59805856, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of D5 (480 mg, 2 mmol), 3-chloro-6-trifluoromethylpyridazine (182 mg, 1 mmol) and diisopropylethylamine (260 mg, 2 mmol) in n-butanol (4 ml) was heated at 190° C. in a microwave reactor (Emrys Optimizer; 0-9 Barr) for 2 h. After this period, the reaction mixture was evaporated in vacuo and the residue extracted with dichloromethane. The organic layer was washed with a saturated solution of sodium hydrogen carbonate, dried (MgSO4) and the solvents evaporated in vacuo. Purification by reverse phase HPLC (conditions as previously described) gave E12 (210 mg, 54%). C18H19F5N4 requires 386; Found 387 (MH+). 1H NMR (CDCl3) δ 1.74 (br.d, J=12.0 Hz, 2H), 1.88 (qd, J=12.0, 3.9 Hz, 2H), 2.17 (td, J=11.8, 2.5 Hz, 2H), 2.96 (br.d, J=11.6 Hz, 2H), 3.00 (s, 3H), 3.47 (s, 2H), 4.85 (t, J=12.1 Hz, 1H), 6.78 (d, J=9.6 Hz, 1H), 6.99-7.05 (m, 1H), 7.10 (dt, J=10.2, 8.1 Hz, 1H), 7.20 (ddd, J=11.4, 7.8, 2.1 Hz, 1H), 7.46 (d, J=9.6 Hz, 1H)

Workup

  1. waitAfter this period
  2. customthe reaction mixture was evaporated in vacuo
  3. extractionthe residue extracted with dichloromethane
  4. washThe organic layer was washed with a saturated solution of sodium hydrogen carbonate
  5. dry with materialdried (MgSO4)
  6. customthe solvents evaporated in vacuo
  7. customPurification by reverse phase HPLC (conditions
  8. customgave E12 (210 mg, 54%)

Sources & evidence

ORD record
ord-ee5605a87c3e496aa2849bf545c908c1
Source dataset
uspto-grants-2015_01
Patent number
US08940743B2

Reaction notes

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