Trifluoroacetic acid → HCID 178475811, compound

HRID 1024086Notes

Reaction equation

HRID 1024086 reaction equation
[C:1]([O:4][CH2:5][C:6]1[C:11]([N:12]2[C:24](=[O:25])[C:23]3[S:22][C:21]4[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=4[C:15]=3[CH2:14][CH2:13]2)=[CH:10][C:9]([F:26])=[CH:8][C:7]=1[C:27]1[N:35]=[C:34]2[C:30]([N:31]=[CH:32][N:33]2COCC[Si](C)(C)C)=[C:29]([NH:44][C:45]2[CH:50]=[CH:49][C:48]([N:51]3[CH2:56][CH2:55][N:54]([CH:57]4[CH2:60][O:59][CH2:58]4)[CH2:53][CH2:52]3)=[CH:47][CH:46]=2)[N:28]=1)(=[O:3])[CH3:2].C(O)(C(F)(F)F)=O>>[C:1]([O:4][CH2:5][C:6]1[C:11]([N:12]2[C:24](=[O:25])[C:23]3[S:22][C:21]4[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=4[C:15]=3[CH2:14][CH2:13]2)=[CH:10][C:9]([F:26])=[CH:8][C:7]=1[C:27]1[N:35]=[C:34]2[C:30]([N:31]=[CH:32][NH:33]2)=[C:29]([NH:44][C:45]2[CH:46]=[CH:47][C:48]([N:51]3[CH2:52][CH2:53][N:54]([CH:57]4[CH2:58][O:59][CH2:60]4)[CH2:55][CH2:56]3)=[CH:49][CH:50]=2)[N:28]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86684157{4-Fluoro-2-[6-({4-[4-(oxetan-3-yl)piperazin-1-yl]phenyl}amino)-9-{[2-(trimethylsilyl)ethoxy]methyl}purin-2-yl]-6-{6-oxo-8-thia-5-azatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-5-yl}phenyl}methyl Acetate

Product 1

HCID 178475811HCID 178475811, compoundYield 60%

Conditions

Temperature
30 °C

Procedure

A mixture of 119a (307 mg, 0.360 mmol) and CF3COOH (5 mL) was stirred at 30° C. for 2 h. The mixture was evaporated in vacuo and the residue was diluted with water (5 mL). The pH of the mixture was adjusted to 7 with saturated NaHCO3 solution and extracted with ethyl acetate (3×10 mL). The combined extract was dried over MgSO4 and evaporated to dryness to afford 119b (150 mg, 60%), which was used in the next step without further purification. MS-ESI: [M+H]+ 723.4

Workup

  1. customThe mixture was evaporated in vacuo
  2. additionthe residue was diluted with water (5 mL)
  3. extractionextracted with ethyl acetate (3×10 mL)
  4. extractionThe combined extract
  5. dry with materialwas dried over MgSO4
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-968fa35c1101420182763e7318800f66
Source dataset
uspto-grants-2014_05
Patent number
US08722676B2

Reaction notes

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