N,N-Diethylethanamine trihydrofluoride → HCID 46870227, compound

HRID 1041909Notes

Reaction equation

HRID 1041909 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:24][C:25](=[O:46])[CH2:26][C:27]2[CH:32]=[CH:31][C:30]([S:33][C:34]3[CH:35]=[CH:36][C:37]4[N:38]([C:40]([CH:43]([CH3:45])[CH3:44])=[N:41][N:42]=4)[CH:39]=3)=[CH:29][CH:28]=2)[N:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][Si](C(C)(C)C)(C)C)=[CH:12][CH:11]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].F.F.F.C(N(CC)CC)C>C1COCC1.CCOC(C)=O>[C:1]([C:5]1[CH:6]=[C:7]([NH:24][C:25](=[O:46])[CH2:26][C:27]2[CH:32]=[CH:31][C:30]([S:33][C:34]3[CH:35]=[CH:36][C:37]4[N:38]([C:40]([CH:43]([CH3:44])[CH3:45])=[N:41][N:42]=4)[CH:39]=3)=[CH:29][CH:28]=2)[N:8]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 175505N,N-Diethylethanamine trihydrofluorideHCID 66977405HCID 66977405, compound

Product 1

HCID 46870227HCID 46870227, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Example 20 step a (80 mg, 0.12 mmol) and triethylamine trihydrofluoride (40 mg, 0.24 mmol) in THF (2 mL) was stirred at RT for 24 H, then diluted with EtOAc, washed with sat. aq. sodium bicarbonate, dried (Na2SO4), and evaporated. The residue was purified by FCC (DCM/MeOH 100/0 to 95/5), dissolved in EtOAc, washed with aq. citric acid and brine, dried (Na2SO4), evaporated and dried in vacuo at 40° C. to afford the title compound (45 mg, 68%) as a pink solid. LCMS (Method 7): Rt 11.15 min, m/z 541 [MH+]. 1H NMR (400 MHz, CDCl3): δ 8.23 (1 H, s), 7.91 (1 H, s), 7.74 (1 H, d, J 9.5), 7.25-7.14 (5 H, m), 7.05 (2 H, d, J 8.4), 6.85 (2 H, t, J 8.6), 6.51 (1 H, s), 3.64 (2 H, s), 3.47-3.38 (1 H, m), 1.55 (3 H, s), 1.53 (3 H, s), 1.31 (9 H, s).

Workup

  1. washwashed with sat. aq. sodium bicarbonate
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customThe residue was purified by FCC (DCM/MeOH 100/0 to 95/5)
  5. dissolutiondissolved in EtOAc
  6. washwashed with aq. citric acid and brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-56feff48126f461cb0cee717d201bf77
Source dataset
uspto-grants-2013_10
Patent number
US08557797B2

Reaction notes

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