Hydrochloric Acid → 5-(2-(1-hydroxy-2,3-dihydro-1H-inden-4-yl)thiazol-5-yl)-2-isopropoxybenzonitrile

HRID 1891496Notes

Reaction equation

HRID 1891496 reaction equation
[Si]([O:8][CH:9]1[C:17]2[C:12](=[C:13]([C:18]3[S:19][C:20]([C:23]4[CH:24]=[CH:25][C:26]([O:31][CH:32]([CH3:34])[CH3:33])=[C:27]([CH:30]=4)[C:28]#[N:29])=[CH:21][N:22]=3)[CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.Cl>O1CCOCC1>[OH:8][CH:9]1[C:17]2[C:12](=[C:13]([C:18]3[S:19][C:20]([C:23]4[CH:24]=[CH:25][C:26]([O:31][CH:32]([CH3:34])[CH3:33])=[C:27]([CH:30]=4)[C:28]#[N:29])=[CH:21][N:22]=3)[CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 583672605-(2-(1-(tert-butyldimethylsilyloxy)-2,3-dihydro-1H-inden-4-yl)thiazol-5-yl)-2-isopropoxy-benzonitrile

Product 1

HCID 532328815-(2-(1-hydroxy-2,3-dihydro-1H-inden-4-yl)thiazol-5-yl)-2-isopropoxybenzonitrileYield 55.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Prepared using General Procedure 3. To crude 5-(2-(1-(tert-butyldimethylsilyloxy)-2,3-dihydro-1H-inden-4-yl)thiazol-5-yl)-2-isopropoxybenzonitrile (0.043 g, 0.095 mmol) was added 4N HCl in dioxane (1.0 mL). The reaction mixture was stirred at room temperature for 2 h. The solvent was concentrated under a stream of N2 and the mixture dissolved in MeOH (1.0 mL). The crude product was purified by preparative HPLC to yield 0.02 g (43%) of 5-(2-(1-hydroxy-2,3-dihydro-1H-inden-4-yl)thiazol-5-yl)-2-isopropoxybenzonitrile 222. LCMS-ESI (m/z): calcd for: C22H20N2O2S: 376.5; found 377.1 [M+H] +, tR=3.31 min.

Workup

  1. customPrepared
  2. concentrationThe solvent was concentrated under a stream of N2
  3. dissolutionthe mixture dissolved in MeOH (1.0 mL)
  4. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-08a100363d444518ae3c543a62cbbd8c
Source dataset
uspto-grants-2013_08
Patent number
US08507538B2

Reaction notes

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