Dichloromethane → HCID 118413252, compound

HRID 929198Notes

Reaction equation

HRID 929198 reaction equation
[CH3:1][C:2]1([O:5][CH2:4]1)[CH3:3].[CH2:6]([N:9]1[C:17]2[C:12](=[N:13][C:14]([C:19]3[CH:24]=[CH:23][C:22]([N:25]4[CH:29]=[C:28]5[CH2:30][NH:31][CH2:32][C:27]5=[N:26]4)=[CH:21][CH:20]=3)=[C:15]([Cl:18])[CH:16]=2)[N:11]=[C:10]1[O:33][C@H:34]1[C@H:38]2[O:39][CH2:40][C@@H:41]([OH:42])[C@H:37]2[O:36][CH2:35]1)[CH:7]=[CH2:8].[NH4+].[OH-].CO.C(Cl)Cl>O1CCOCC1.CO.C(Cl)Cl>[CH2:6]([N:9]1[C:17]2[C:12](=[N:13][C:14]([C:19]3[CH:20]=[CH:21][C:22]([N:25]4[CH:29]=[C:28]5[CH2:30][N:31]([CH2:1][C:2]([OH:5])([CH3:4])[CH3:3])[CH2:32][C:27]5=[N:26]4)=[CH:23][CH:24]=3)=[C:15]([Cl:18])[CH:16]=2)[N:11]=[C:10]1[O:33][C@H:34]1[C@H:38]2[O:39][CH2:40][C@@H:41]([OH:42])[C@H:37]2[O:36][CH2:35]1)[CH:7]=[CH2:8]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11208Isobutylene oxide2×HCID 21894508Ammonium hydroxide methanolHCID 90067288HCID 90067288, compound

Product 1

HCID 118413252HCID 118413252, compound

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
80 °C

Procedure

Isobutylene oxide (17 μl, 0.191 mmol) was added to a stirred solution of (3R,3aR,6R,6aR)-6-[1-allyl-6-chloro-5-[4-(5,6-dihydro-4H-pyrrolo[3,4-c]pyrazol-2-yl)phenyl]imidazo[4,5-b]pyridin-2-yl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol (83.4 mg, 0.160 mmol) in dioxane (0.64 ml). The reaction mixture was a pale yellow solution that was heated to 80° C. After 3 days, additional isobutylene oxide (8 μl, 0.090 mmol) was added. After stirring an additional 16 h, the reaction mixture was cooled to room temperature. The reaction mixture was then diluted with MeOH/DCM and loaded onto two 500 micron 20 cm×20 cm silica gel plates, which were developed twice using 10% (10% NH4OH/MeOH)/DCM. The silica containing the product band was collected and eluted with 10% (10% NH4OH/MeOH)/DCM (80 ml). The solvent was evaporated under reduced pressure to give the desired product as a yellow residue. LC-MS: calculated for C30H33ClN6O5 592.22 observed m/e: 593.25 (M+H)+ (Rt 1.00/2 min)

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. customThe silica containing the product band was collected
  3. washeluted with 10% (10% NH4OH/MeOH)/DCM (80 ml)
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-98f4f92d3c724cfe84d6aaf964779b4a
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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