Triethylamine → HCID 86687110, compound

HRID 1402265Notes

Reaction equation

HRID 1402265 reaction equation
[CH:1]([Si:4](Cl)([CH:8]([CH3:10])[CH3:9])[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[F:12][C:13]1[CH:14]=[CH:15][C:16]2[N:17]([C:19]([C@@H:22]3[CH2:26][CH2:25][CH2:24][N:23]3[CH2:27][CH2:28][CH2:29][OH:30])=[N:20][N:21]=2)[CH:18]=1.CCN(CC)CC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[F:12][C:13]1[CH:14]=[CH:15][C:16]2[N:17]([C:19]([C@@H:22]3[CH2:26][CH2:25][CH2:24][N:23]3[CH2:27][CH2:28][CH2:29][O:30][Si:4]([CH:8]([CH3:10])[CH3:9])([CH:5]([CH3:7])[CH3:6])[CH:1]([CH3:3])[CH3:2])=[N:20][N:21]=2)[CH:18]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 139400Triisopropylsilyl chlorideHCID 86687111HCID 86687111, compound

Product 1

HCID 86687110HCID 86687110, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Triisopropylsilyl chloride (266 μ□L, 1.24 mmol) was added to a solution of Intermediate 84e (218 mg, 0.82 mmol) and Et3N (26 μ□L, 1.24 mmol) in DCM (8.00 mL). The reaction was stirred overnight then 4-(dimethylamino)pyridine (10.0 mg, 0.082 mmol) added. The reaction was stirred for 3 h then partitioned between EtOAc and water. The aqueous layer was then extracted with EtOAc (3×). The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated in vacuo. The residue was purified by FCC, using 0-7.5% [2M NH3 in MeOH] in DCM, to give the title compound (317 mg, 92%). 1H NMR (300 MHz, CDCl3): 0.92 (2H, s), 1.56-1.68 (2H, m), 1.89-2.10 (3H, m), 2.21-2.40 (3H, m), 2.56 (1H, dt, J 12.1, 7.9), 3.40 (1H, m), 3.46-3.64 (2H, m), 4.22 (1H, t, J 8.4), 7.16 (1H, ddd, J 9.9, 7.5, 2.3), 7.71 (1H, ddd, J 10.0, 4.9, 0.6), 8.64 (1H, m).

Workup

  1. stirringThe reaction was stirred for 3 h
  2. customthen partitioned between EtOAc and water
  3. extractionThe aqueous layer was then extracted with EtOAc (3×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was purified by FCC

Sources & evidence

ORD record
ord-0ab22425e95149c5b678161327766bc7
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

Loading…