N,N-Diethylethanamine trihydrofluoride → HCID 118045245, compound

HRID 596121Notes

Reaction equation

HRID 596121 reaction equation
[C:1]([O:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([C:16]2[N:21]=[C:20]([C:22]3[CH:34]=[CH:33][C:25]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[C:24]([F:35])[CH:23]=3)[C:19]([N:36]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[N:18][CH:17]=2)[CH2:12][C:11]1=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[B-](F)(F)(F)F.CCN([S+](F)F)CC.[FH:65].[FH:66].F.C(N(CC)CC)C>C(Cl)Cl>[C:1]([O:9][CH:10]1[CH2:15][CH2:14][CH:13]([C:16]2[N:21]=[C:20]([C:22]3[CH:34]=[CH:33][C:25]([C:26]([O:28][C:29]([CH3:30])([CH3:32])[CH3:31])=[O:27])=[C:24]([F:35])[CH:23]=3)[C:19]([N:36]([C:37]([O:39][C:40]([CH3:41])([CH3:43])[CH3:42])=[O:38])[C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])=[N:18][CH:17]=2)[CH2:12][C:11]1([F:66])[F:65])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 175505N,N-Diethylethanamine trihydrofluorideHCID 44517918(Diethylamino)(difluoro)sulfanium tetrafluoroborateHCID 118046545HCID 118046545, compound

Product 1

HCID 118045245HCID 118045245, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(6-((1S,45)-4-(benzoyloxy)-3-oxocyclohexyl)-3-(bis(tert-butoxycarbonyl)amino)pyrazin-2-yl)-2-fluorobenzoate (730 mg, 1.034 mmol) in DCM (7 mL) at RT was added XtalFlour-E (939 mg, 4.14 mmol) followed by triethylamine trihydrofluoride (0.674 mL, 4.14 mmol). The resultant mixture was stirred at RT for 5 hours. The mixture was filtered and the filtered solution was directly applied for ISCO separation: 24 g silica gel, 0 to 70% EtOAc in Heptane, 30 min. A light yellow solid (670 mg, 0.902 mmol, 87% yield) was obtained. LC-MS (m/z): (MH+) 728.0 at 0.95 min (non-polar MS method). 1H NMR (400 MHz, CDCl3) δ ppm 0.88 (s, 2H) 1.19-1.39 (m, 21H) 1.48-1.68 (m, 11H) 1.86-2.08 (m, 2H) 2.08-2.21 (m, 1H) 2.26-2.47 (m, 2H) 2.47-2.63 (m, 1H) 3.21-3.44 (m, 1H) 5.22-5.51 (m, 1H) 7.41-7.55 (m, 4H) 7.60 (s, 1H) 7.96 (d, J=7.82 Hz, 1H) 8.06-8.19 (m, 2H) 8.42 (s, 1H).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtered solution was directly applied for ISCO separation
  3. custom24 g silica gel, 0 to 70% EtOAc in Heptane, 30 min

Sources & evidence

ORD record
ord-fe08e272d9834283bc3a41e86ec78791
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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