Boron trifluoride etherate → HCID 86695118, compound

HRID 1503944Notes

Reaction equation

HRID 1503944 reaction equation
COC(OC)[CH2:4][C@H:5]1[CH2:16][CH2:15][C:14]2[S:13][C:12]3[N:11]=[CH:10][N:9]=[C:8]([O:17][CH:18]4[CH2:23][CH2:22][CH:21]([N:24]([CH3:32])C(=O)OC(C)(C)C)[CH2:20][CH2:19]4)[C:7]=3[C:6]1=2.[Si]([C:39]#[N:40])(C)(C)C.B(F)(F)F.C[CH2:46][O:47][CH2:48]C>C(Cl)Cl>[CH3:46][O:47][CH:48]([CH2:4][C@H:5]1[CH2:16][CH2:15][C:14]2[S:13][C:12]3[N:11]=[CH:10][N:9]=[C:8]([O:17][CH:18]4[CH2:23][CH2:22][CH:21]([NH:24][CH3:32])[CH2:20][CH2:19]4)[C:7]=3[C:6]1=2)[C:39]#[N:40]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 82115Trimethylsilyl cyanideHCID 68115506HCID 68115506, compound

Product 1

HCID 86695118HCID 86695118, compoundYield 979.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 100-mL 3-necked round-bottom flask was placed a solution of tert-butyl N-(4-[[(3R)-3-(2,2-dimethoxyethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]cyclohexyl)-N-methylcarbamate (470 mg, 0.96 mmol, 1.00 equiv) in distilled DCM (15 mL). TMSCN (474 mg) and BF3.Et2O (15 mg) were added via syringe under nitrogen at 0° C. The resulting solution was stirred for 3 hr in a water/ice bath. After completion, the reaction was quenched with saturated aqueous NaHCO3 and extracted with 3×50 mL of ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum to afford the desired 2-methoxy-3-[(3R)-12-[[4-(methylamino)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-3-yl]propanenitrile (400 mg, crude) as a yellow oil. MS (ES): m/z 387 [M+H]+.

Workup

  1. customInto a 100-mL 3-necked round-bottom flask was placed
  2. customAfter completion, the reaction was quenched with saturated aqueous NaHCO3
  3. extractionextracted with 3×50 mL of ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-296c01422f5248078c7a31b699d207ab
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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