Triethylsilane → HCID 66614157, compound

HRID 510137Notes

Reaction equation

HRID 510137 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[C:14](=[O:15])[N:13]([CH2:16][CH2:17][O:18][CH3:19])[C:12]2[C:7]1=[N:8][C:9]([C:20]1[C:28]3[C:23](=[N:24][CH:25]=[CH:26][CH:27]=3)[N:22]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[F:36])[N:21]=1)=[N:10][CH:11]=2.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[F:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[CH2:29][N:22]1[C:23]2=[N:24][CH:25]=[CH:26][CH:27]=[C:28]2[C:20]([C:9]2[N:8]=[C:7]3[C:12]([N:13]([CH2:16][CH2:17][O:18][CH3:19])[C:14](=[O:15])[NH:6]3)=[CH:11][N:10]=2)=[N:21]1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 66614128HCID 66614128, compound

Product 1

HCID 66614157HCID 66614157, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

317 mg (0.501 mmol) of the compound from example 83A were dissolved in 15 ml of trifluoroacetic acid, 582 mg (5.009 mmol) of triethylsilane were added and the mixture was heated to reflux for 18 h. The reaction mixture was partitioned between 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). 167 mg of the title compound were obtained (79% of theory).

Workup

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

Sources & evidence

ORD record
ord-30536b820a0f4be8bd25b991470062f4
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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