Hydrochloric Acid → 2-[(1R)-5-(5-Ethylpyrimidin-2-yl)-2,3-dihydro-1H-inden-1-yl]-2,7-diazaspiro[3.5]nonane dihydrochloride

HRID 1913453Notes

Reaction equation

HRID 1913453 reaction equation
[CH2:1]([C:3]1[CH:4]=[N:5][C:6]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[C@H:14]([N:18]2[CH2:21][C:20]4([CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]4)[CH2:19]2)[CH2:13][CH2:12]3)=[N:7][CH:8]=1)[CH3:2].[ClH:34].CO>O1CCOCC1>[ClH:34].[ClH:34].[CH2:1]([C:3]1[CH:4]=[N:5][C:6]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[C@H:14]([N:18]2[CH2:21][C:20]4([CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)[CH2:19]2)[CH2:13][CH2:12]3)=[N:7][CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 58438491tert-butyl 2-[(1R)-5-(5-ethylpyrimidin-2-yl)-2,3-dihydro-1H-inden-1-yl]-2,7-diazaspiro[3.5]nonane-7-carboxylate

Product 1

HCID 674091552-[(1R)-5-(5-Ethylpyrimidin-2-yl)-2,3-dihydro-1H-inden-1-yl]-2,7-diazaspiro[3.5]nonane dihydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a flask charged with tert-butyl 2-[(1R)-5-(5-ethylpyrimidin-2-yl)-2,3-dihydro-1H-inden-1-yl]-2,7-diazaspiro[3.5]nonane-7-carboxylate (3-1b, 583 mg, 1.39 mmol) was added 8.0 mL of 4N HCl in dioxane at room temperature. A yellow precipitate formed immediately after the addition. The mixture was stirred at room temperature for 40 minutes. Anhydrous methanol (4 mL) was added to solublize the reaction. The resulting solution was stirred at room temperature for 4 hours. Solvent and excess HCl were removed and dried in vacuo to afford 630 mg (100%) of a light yellow solid (3-1c). The crude product was taken on to the next step without further purification. MS (ES+) 349.4 (M+H)+. 1H NMR (CD3OD) δ 1.40 (t, 3H) 2.21-2.28 (m, 5H) 2.61 (br s, 1H) 2.93 (q, 2H) 3.16-3.34 (m, 4H), 3.38-3.51 (m, 1H), 4.12-4.29 (m, 4H) 4.52-4.56 (m, 1H) 5.08-5.12 (m, 1H) 7.89-7.93 (m, 1H) 8.29-8.33 (m, 2H), 9.15-9.19 (m, 2H).

Workup

  1. customA yellow precipitate formed immediately
  2. additionafter the addition
  3. customthe reaction
  4. stirringThe resulting solution was stirred at room temperature for 4 hours
  5. customSolvent and excess HCl were removed
  6. customdried in vacuo

Sources & evidence

ORD record
ord-c14987e7e44341189ee711d8f69cdabe
Source dataset
uspto-grants-2013_12
Patent number
US08609680B2

Reaction notes

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