Hydrochloric Acid → HCID 57526807, compound

HRID 1452630Notes

Reaction equation

HRID 1452630 reaction equation
[C:1]([O:5][C:6](=[O:32])[N:7]([C:17]1[N:22]2[N:23]=[CH:24][CH:25]=[C:21]2[N:20]=[C:19]([Cl:26])[C:18]=1[CH2:27][CH:28]([OH:31])[CH2:29][OH:30])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH3:16])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:40]([Si:44](Cl)([CH3:46])[CH3:45])([CH3:43])([CH3:42])[CH3:41].Cl>C(Cl)Cl>[Si:44]([O:30][CH2:29][CH:28]([OH:31])[CH2:27][C:18]1[C:19]([Cl:26])=[N:20][C:21]2[N:22]([N:23]=[CH:24][CH:25]=2)[C:17]=1[N:7]([C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:15][CH3:16])=[CH:12][CH:13]=1)[C:6](=[O:32])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:46])[CH3:45]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 57526836HCID 57526836, compound

Product 1

HCID 57526807HCID 57526807, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a methylene chloride (3.6 mL) solution containing tert-butyl[5-chloro-6-(2,3-dihydroxypropyl)pyrazolo[1,5-a]pyrimidin-7-yl](4-ethoxyphenyl)carbamate (500 mg, 1.08 mmol), triethylamine (300 μL, 2.16 mmol), tert-butylchlorodimethylsilane (195 mg, 1.30 mmol) and N,N-dimethylpyridine (13 mg, 0.108 mmol) were added. After the reaction mixture was stirred at room temperature for 5 hr, 1 mol/L hydrochloric acid was added here, and the mixture was extracted with ethyl acetate. The combined ethyl acetate layer was washed with aqueous sodium hydrogen carbonate and then brine and dried over sodium sulfate. After the sodium sulfate was filtered off, the solvent was distilled off and the residue was purified with column chromatography to obtain the title compound (503 mg).

Workup

  1. additionwere added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined ethyl acetate layer was washed with aqueous sodium hydrogen carbonate
  4. dry with materialbrine and dried over sodium sulfate
  5. filtrationAfter the sodium sulfate was filtered off
  6. distillationthe solvent was distilled off
  7. customthe residue was purified with column chromatography

Sources & evidence

ORD record
ord-678791da6f7f4bba8f60b34119a4f4cf
Source dataset
uspto-grants-2009_01
Patent number
US07473694B2

Reaction notes

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