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Potassium Phosphate, Tribasic → HCID 131735087, compound

HRID 929147
Notes
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Reaction equation

HRID 929147 reaction equation
[CH2:1]([N:4]1[C:12]2[C:7](=[N:8][C:9]([C:14]3[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=3)=[C:10]([Cl:13])[CH:11]=2)[N:6]=[C:5]1[O:21][C@@H:22]1[CH2:26][O:25][C@@H:24]2[C@H:27]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[CH2:28][O:29][C@H:23]12)[CH:2]=[CH2:3].[N:38]1[NH:39][CH:40]=[C:41]2[CH2:45][N:44]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH2:43][C:42]=12.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CN[C@@H]1CCCC[C@H]1NC>[Cu]I.CCOC(C)=O.CCCCCC.O1CCOCC1>[Si:31]([O:30][C@H:27]1[C@H:24]2[O:25][CH2:26][C@@H:22]([O:21][C:5]3[N:4]([CH2:1][CH:2]=[CH2:3])[C:12]4[C:7]([N:6]=3)=[N:8][C:9]([C:14]3[CH:15]=[CH:16][C:17]([N:39]5[CH:40]=[C:41]6[CH2:45][N:44]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH2:43][C:42]6=[N:38]5)=[CH:18][CH:19]=3)=[C:10]([Cl:13])[CH:11]=4)[C@H:23]2[O:29][CH2:28]1)([C:34]([CH3:35])([CH3:36])[CH3:37])([CH3:32])[CH3:33]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 90067172HCID 90067172, compoundHCID 178451520HCID 178451520, compound

Product 1

HCID 131735087HCID 131735087, compound

Reagents, catalysts & solvents 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 312751,4-DioxaneSolvent
HCID 21226206Ethyl acetate hexaneSolvent2×

Conditions

Temperature
100 °C

Procedure

A vial was charged with [(3R,3aR,6R,6aS)-3-[1-allyl-5-(4-bromophenyl)-6-chloro-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 (508.1 mg, 0.837 mmol), tert-butyl 4,6-dihydro-2H-pyrrolo[3,4-c]pyrazole-5-carboxylate (213.1 mg, 1.018 mmol), tripotassium phosphate (603.1 mg, 2.84 mmol), and copper(I) iodide (33.2 mg, 0.174 mmol). The vial was evacuated and backfilled with nitrogen (3×). Trans-N,N′-dimethylcyclohexane-1,2-diamine (53 μl, 0.335 mmol) and dioxane (1.6 ml) were added to the vial to give a pale blue suspension that was heated at 100° C. with stirring for 24 h. The reaction mixture was cooled to room temperature and partitioned between EtOAc (100 ml) and water (100 ml). The aqueous layer was extracted with EtOAc (2×50 ml). The organic layers were combined, washed with brine (1×30 ml), dried over MgSO4, filtered, and evaporated under reduced pressure to give a light green residue. Flash chromatography of the residue utilizing an 40 g silica RediSep Rf® column and employing a 0-40% EtOAc/hexane gradient followed by 40% EtOAc/hexane afforded the desired product as a white foam. LC-MS: calculated for C37H47ClN6O6Si 734.3 observed m/e: 735.34 (M+H)+ (Rt 1.47/2 min)

Workup

  1. customThe vial was evacuated
  2. customto give a pale blue suspension that
  3. temperatureThe reaction mixture was cooled to room temperature
  4. custompartitioned between EtOAc (100 ml) and water (100 ml)
  5. extractionThe aqueous layer was extracted with EtOAc (2×50 ml)
  6. washwashed with brine (1×30 ml)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customto give a light green residue

Sources & evidence

ORD record
ord-105129ceb7b047ae8a9f9a2274df99a0
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09290517B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes