Hydrochloric Acid → HCID 72202968, compound

HRID 1482937Notes

Reaction equation

HRID 1482937 reaction equation
[Si]([O:8][CH2:9][CH2:10][O:11][C:12]1[C:13]([NH:34][C:35]2[C:40]([C:41]#[N:42])=[CH:39][N:38]=[CH:37][CH:36]=2)=[N:14][C:15]([C:18]2[C:19]3[CH2:33][CH2:32][CH2:31][C:20]=3[N:21]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[F:30])[N:22]=2)=[N:16][CH:17]=1)(C(C)(C)C)(C)C.Cl>O1CCOCC1>[F:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:23][N:21]1[C:20]2[CH2:31][CH2:32][CH2:33][C:19]=2[C:18]([C:15]2[N:14]=[C:13]([NH:34][C:35]3[C:40]([C:41]#[N:42])=[CH:39][N:38]=[CH:37][CH:36]=3)[C:12]([O:11][CH2:10][CH2:9][OH:8])=[CH:17][N:16]=2)=[N:22]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 123859023HCID 123859023, compound

Product 1

HCID 72202968HCID 72202968, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

32.7 mg of 4-({5-(2-{[tert-butyl(dimethyl)silyl]oxy}ethoxy)-2-[1-(2-fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]pyrazol-3-yl]pyrimidin-4-yl}amino)nicotinonitrile 2-3-10 (0.034 mmol, 1.00 eq.) were dissolved in 0.58 mL dioxane and 0.085 mL 4 M hydrochloric acid in dioxane (0.341 mmol, 10.0 eq.) were added and stirred at rt over night. The reaction mixture was partitioned between half saturated aqueous ammonium chloride solution and DCM/isopropanol (4:1). The combined organic layers were washed with brine, dried over silicon filter and concentrated in vacuo. The residue was purified by preparative thin layer chromatography (DCM/methanol (9:1)) to provide 8.7 mg (0.02 mmol, 54%) of analytically pure target compound.

Workup

  1. customThe reaction mixture was partitioned between half saturated aqueous ammonium chloride solution and DCM/isopropanol (4:1)
  2. washThe combined organic layers were washed with brine
  3. customdried over silicon
  4. filtrationfilter
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative thin layer chromatography (DCM/methanol (9:1))
  7. customto provide 8.7 mg (0.02 mmol, 54%) of analytically pure target compound

Sources & evidence

ORD record
ord-eaf74374fd63472db3277420fdd65327
Source dataset
uspto-grants-2016_08
Patent number
US09416125B2

Reaction notes

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