Triethylsilane → HCID 66635174, compound

HRID 510144Notes

Reaction equation

HRID 510144 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[C:10]2[N:11]=[C:12]([C:15]3[C:23]4[C:18](=[N:19][CH:20]=[C:21]([F:24])[CH:22]=4)[N:17]([CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[F:32])[N:16]=3)[N:13]=[CH:14][C:9]=2[N:8]([CH3:33])[S:7]1(=[O:35])=[O:34].C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[F:24][C:21]1[CH:22]=[C:23]2[C:15]([C:12]3[N:13]=[CH:14][C:9]4[N:8]([CH3:33])[S:7](=[O:34])(=[O:35])[NH:6][C:10]=4[N:11]=3)=[N:16][N:17]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[F:32])[C:18]2=[N:19][CH:20]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 66634917HCID 66634917, compound

Product 1

HCID 66635174HCID 66635174, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

28 mg (0.050 mmol) of the compound from example 100A were dissolved in 1.5 ml of trifluoroacetic acid and then admixed with 79 μl (0.495 mmol) of triethylsilane, and the mixture was heated to reflux overnight. This was followed by concentration to dryness. After purification by means of preparative HPLC (acetonitrile:water (+0.05% formic acid) gradient), this gave 10.4 mg (48% of theory) of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. concentrationThis was followed by concentration to dryness
  4. customAfter purification by means of preparative HPLC (acetonitrile:water (+0.05% formic acid) gradient)

Sources & evidence

ORD record
ord-11dc3467c9e14bc6bb633252a589f161
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

Loading…