Triethylamine → HCID 131735106, compound

HRID 929234Notes

Reaction equation

HRID 929234 reaction equation
C(N(CC)CC)C.FC(F)(F)C(O)=O.[CH2:15]([N:18]1[C:26]2[C:21](=[N:22][C:23]([N:28]3[CH:32]=[C:31]4[CH2:33][NH:34][CH2:35][C:30]4=[N:29]3)=[C:24]([Cl:27])[CH:25]=2)[N:20]=[C:19]1[O:36][C@@H:37]1[CH2:41][O:40][C@@H:39]2[C@H:42]([O:45][Si:46]([C:49]([CH3:52])([CH3:51])[CH3:50])([CH3:48])[CH3:47])[CH2:43][O:44][C@H:38]12)[CH:16]=[CH2:17].[CH3:53][S:54](Cl)(=[O:56])=[O:55]>C(Cl)Cl.CCOC(C)=O.O.Cl>[CH2:15]([N:18]1[C:26]2[C:21](=[N:22][C:23]([N:28]3[CH:32]=[C:31]4[CH2:33][N:34]([S:54]([CH3:53])(=[O:56])=[O:55])[CH2:35][C:30]4=[N:29]3)=[C:24]([Cl:27])[CH:25]=2)[N:20]=[C:19]1[O:36][C@@H:37]1[CH2:41][O:40][C@@H:39]2[C@H:42]([O:45][Si:46]([C:49]([CH3:52])([CH3:51])[CH3:50])([CH3:47])[CH3:48])[CH2:43][O:44][C@H:38]12)[CH:16]=[CH2:17]

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 131735104HCID 131735104, compound

Product 1

HCID 131735106HCID 131735106, compound

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (91 uL, 0.653 mmol) was added to a ice cold mixture of [(3R,3aR,6R,6aS)-3-[1-allyl-6-chloro-5-(5,6-dihydro-4H-pyrrolo[3,4-c]pyrazol-2-yl)imidazo[4,5-b]pyridin-2-yl]oxy-2,3,3a,5,6,6a-hexahydrofuro-[3,2-b]furan-6-yl]oxy-tert-butyl-dimethyl-silane 2,2,2-trifluoroacetic acid (86.4 mg, 0.128 mmol) and methane sulfonyl chloride (16 uL, 0.205 mmol) in DCM (1.0 ml). After 20 minutes, the reaction mixture was diluted with EtOAc (30 ml), water (20 ml) and 2N HCl (2 mL). The EtOAc layer was washed with brine (10 mL), dried over MgSO4, filtered, and evaporated under reduced pressure to give an oil. The oil was purified on preparative silica plates (2×1000 u developed with 1:1 EtOAc/hexanes) to give the title compound. LC-MS: calculated for C27H37ClN6O6SSi 636.20 observed m/e: 637.13 (M+H)+ (Rt 1.35/2 min)

Workup

  1. washThe EtOAc layer was washed with brine (10 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customto give an oil
  6. customThe oil was purified on preparative silica plates (2×1000 u developed with 1:1 EtOAc/hexanes)

Sources & evidence

ORD record
ord-6519766d814e4ea0ab0a3bf64969b0f0
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

Loading…