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

HRID 600818Notes

Reaction equation

HRID 600818 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-dc13849444364ed3a9d733ab41a6654b
Source dataset
uspto-grants-2011_03
Patent number
US07902236B2

Reaction notes

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