(1-Bromo-2,2-dimethoxyethyl)benzene → 8-(5-Phenylthiazol-2-ylamino)-1,2,3,4-tetrahydronaphthalen-2-ol

HRID 1785581Notes

Reaction equation

HRID 1785581 reaction equation
[Si]([O:8][CH:9]1[CH2:18][C:17]2[C:16]([NH:19][C:20]([NH2:22])=[S:21])=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.Br[CH:24]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH:25](OC)OC>CCO.Cl>[C:30]1([C:24]2[S:21][C:20]([NH:19][C:16]3[CH:15]=[CH:14][CH:13]=[C:12]4[C:17]=3[CH2:18][CH:9]([OH:8])[CH2:10][CH2:11]4)=[N:22][CH:25]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 2

HCID 11064658(1-Bromo-2,2-dimethoxyethyl)benzeneHCID 86609617[7-(tert-Butyldimethylsilyloxy)-5,6,7,8-tetrahydronaphthalen-1-yl]thiourea

Product 1

HCID 119643218-(5-Phenylthiazol-2-ylamino)-1,2,3,4-tetrahydronaphthalen-2-ol

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of the product of Example 24A (200 mg, 0.594 mmol) and the product of Example 24B (146 mg, 0.596 mmol) was refluxed for 2 hours in a mixture of EtOH (6 mL) and 1N HCl (1 mL). After cooling to room temperature, the mixture was quenched with saturated NaHCO3 solution and was extracted with EtOAc. The extracts were dried over Na2SO4, filtered evaporated under reduced pressure, and chromatographed on silica gel (95:5 to 92:8 CH2Cl2:CH3OH eluant). The title compound was afforded as a pale tan solid, 53 mg (28%). 1H NMR (DMSO-d6) δ 9.29 (s, 1H), 7.57 (m, 2H), 7.46-7.49 (m, 2H), 7.33-7.38 (m, 2H), 7.22 (m, 1H), 7.10 (m, 1H), 6.88 (d, J=7.4 Hz, 1H), 4.82 (d, J=4.0 Hz, 1H), 3.82 (m, 1H), 2.71-2.98 (m, 4H), 1.83-1.93 (m, 1H), 1.57-1.66 (m, 1H). MS (ESI+) m/z 323 (M+H). Anal. calcd. For C19H18N2OS: C, 70.78; H, 5.63; N, 8.69. Found: C, 70.91; H, 5.37; N, 8.33.

Workup

  1. customthe mixture was quenched with saturated NaHCO3 solution
  2. extractionwas extracted with EtOAc
  3. dry with materialThe extracts were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customchromatographed on silica gel (95:5 to 92:8 CH2Cl2:CH3OH eluant)

Sources & evidence

ORD record
ord-437a814e1d3a49be80a33c254539f270
Source dataset
uspto-grants-2009_03
Patent number
US07504520B2

Reaction notes

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