Water → HCID 86720057, compound

HRID 510140Notes

Reaction equation

HRID 510140 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[C:14](=[O:15])[N:13]([CH2:16][C:17]([F:23])([F:22])[C:18]([F:21])([F:20])[F:19])[C:12]2[C:7]1=[N:8][C:9]([C:24]1[C:32]3[C:27](=[N:28][CH:29]=[CH:30][CH:31]=3)[N:26]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[F:40])[N:25]=1)=[N:10][CH:11]=2.C([SiH](CC)CC)C.O.C(=O)([O-])O.[Na+]>FC(F)(F)C(O)=O.C(OCC)(=O)C>[F:40][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=1[CH2:33][N:26]1[C:27]2=[N:28][CH:29]=[CH:30][CH:31]=[C:32]2[C:24]([C:9]2[N:8]=[C:7]3[C:12]([N:13]([CH2:16][C:17]([F:22])([F:23])[C:18]([F:19])([F:20])[F:21])[C:14](=[O:15])[NH:6]3)=[CH:11][N:10]=2)=[N:25]1

Participants

7

Reactant 4

HCID 962WaterHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 86720058HCID 86720058, compound

Product 1

HCID 86720057HCID 86720057, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Procedure

471 mg (0.60 mmol) of the compound from example 85A were dissolved in 15 ml of trifluoroacetic acid, 698 mg (6.01 mmol) of triethylsilane were added and the mixture was heated to reflux for 18 h. The reaction mixture was admixed with water and ethyl acetate, and neutralized with saturated aqueous sodium hydrogencarbonate solution. The organic phase was dried over sodium sulfate and concentrated on a rotary evaporator. The residue was dried under high vacuum, and purified by means of preparative HPLC (eluent: methanol/water with 0.1% trifluoroacetic acid, gradient 30:70→90:10). 252 mg of the title compound were obtained (85% of theory).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 18 h
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated on a rotary evaporator
  5. customThe residue was dried under high vacuum
  6. custompurified by means of preparative HPLC (eluent: methanol/water with 0.1% trifluoroacetic acid, gradient 30:70→90:10)

Sources & evidence

ORD record
ord-33b9055b3ec145669411762c9de5a9d2
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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