Hydrochloric Acid → N1-(5-p-methylphenyloxazol-2-yl)-5,6,7,8-tetrahydronaphthalene-1,7-diamine

HRID 1785572

Reaction equation

HRID 1785572 reaction equation
Cl.C(OC(=O)[NH:8][CH:9]1[CH2:18][CH2:17][C:16]2[C:11](=[C:12]([NH:19][C:20]3[O:21][C:22]([C:25]4[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=4)=[CH:23][N:24]=3)[CH:13]=[CH:14][CH:15]=2)[CH2:10]1)(C)(C)C>O1CCOCC1>[CH3:31][C:28]1[CH:29]=[CH:30][C:25]([C:22]2[O:21][C:20]([NH:19][C:12]3[C:11]4[CH2:10][CH:9]([NH2:8])[CH2:18][CH2:17][C:16]=4[CH:15]=[CH:14][CH:13]=3)=[N:24][CH:23]=2)=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67229286[8-(5-p-Methylphenyloxazol-2-ylamino)-1,2,3,4-tetrahydronaphthalen-2-yl]carbamic acid tert-butyl ester

Product 1

HCID 11964240N1-(5-p-methylphenyloxazol-2-yl)-5,6,7,8-tetrahydronaphthalene-1,7-diamine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Hydrogen chloride in dioxane (4N, 7 mL, 28 mmol) was added to a suspension of 199 mg (0.474 mmol) of the product of Example 20G in 1 mL dioxane. After stirring 45 minutes, the mixture was quenched with 3N NaOH solution, then diluted with EtOAc and poured into water. The separated organic phase was washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude product was triturated with Et2O and the solid was collected by vacuum filtration. The result was 92 mg (61%) of the title compound as a pale pink solid. 1H NMR (DMSO-d6) δ 9.02 (br s, 1H), 7.57 (d, J=7.1 Hz, 1H), 7.45 (d, J=8.1 Hz, 2H), 7.28 (s, 1H), 7.23 (d, J=8.1 Hz, 2H), 7.08 (t, J=7.8 Hz, 1H), 6.83 (d, J=7.1 Hz, 1H), 3.05-2.70 (m, 4H), 2.31 (m, 4H), 1.85 (m, 3H), 1.42 (m, 1H); MS (ESI+) m/z 320 (M+H)+.

Workup

  1. customthe mixture was quenched with 3N NaOH solution
  2. additiondiluted with EtOAc
  3. additionpoured into water
  4. washThe separated organic phase was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was triturated with Et2O
  9. filtrationthe solid was collected by vacuum filtration

Sources & evidence

ORD record
ord-cc026df84b014b2786546b5466938416
Source dataset
uspto-grants-2009_03
Patent number
US07504520B2

Linked notes

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