Tetrahydrofuran → HCID 135999744, compound

HRID 1157954Notes

Reaction equation

HRID 1157954 reaction equation
[C:1]([O:5][C:6](=[O:54])[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([NH:15][CH:16]([C:29]2[CH:34]=[C:33]([CH2:35][CH3:36])[CH:32]=[C:31]([O:37][CH2:38][CH2:39][O:40][Si](C(C)C)(C(C)C)C(C)C)[C:30]=2[F:51])[C:17]2[NH:21][C:20](=[O:22])[N:19]([C:23]3[N:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[N:18]=2)[CH:12]=[CH:11][C:10]=1[C:52]#[N:53])([CH3:4])([CH3:3])[CH3:2].C1COCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>O>[C:1]([O:5][C:6](=[O:54])[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([NH:15][CH:16]([C:29]2[CH:34]=[C:33]([CH2:35][CH3:36])[CH:32]=[C:31]([O:37][CH2:38][CH2:39][OH:40])[C:30]=2[F:51])[C:17]2[NH:21][C:20](=[O:22])[N:19]([C:23]3[N:24]=[CH:25][CH:26]=[CH:27][N:28]=3)[N:18]=2)[CH:12]=[CH:11][C:10]=1[C:52]#[N:53])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 135999749HCID 135999749, compound

Product 1

HCID 135999744HCID 135999744, compoundYield 125.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of [2-cyano-5-({[5-ethyl-2-fluoro-3-(2-triisopropylsilanyloxyethoxy)phenyl]-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl}amino)benzyl]carbamic acid t-butyl ester (56 mg) and THF (4 mL) there was added a 1M THF solution of tetrabutylammonium fluoride (0.147 mL). The mixture was stirred for 4 hours, and then ethyl acetate (50 mL) and water (50 mL) were added. The mixture was sufficiently shaken, and then the organic layer was separated off, washed twice with water (50 mL) and once with saturated aqueous sodium chloride (50 mL) in that order, and dried over anhydrous magnesium sulfate. The mixture was filtered to obtain a filtrate and the solvent in the filtrate was distilled off under reduced pressure to obtain the target compound (56 mg) as a colorless oil.

Workup

  1. stirringThe mixture was sufficiently shaken
  2. customthe organic layer was separated off
  3. washwashed twice with water (50 mL) and once with saturated aqueous sodium chloride (50 mL) in that order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe mixture was filtered
  6. customto obtain a filtrate
  7. distillationthe solvent in the filtrate was distilled off under reduced pressure

Sources & evidence

ORD record
ord-dc67cdcc54c14720a8c01805f9576464
Source dataset
uspto-grants-2010_10
Patent number
US07807690B2

Reaction notes

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