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

HRID 1913455Notes

Reaction equation

HRID 1913455 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C@H:12]([N:16]1[CH2:19][C:18]3([CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]3)[CH2:17]1)[CH2:11][CH2:10]2.[ClH:32].CO>O1CCOCC1>[ClH:32].[ClH:32].[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C@@H:12]([N:16]1[CH2:17][C:18]3([CH2:20][CH2:21][NH:22][CH2:23][CH2:24]3)[CH2:19]1)[CH2:11][CH2:10]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 67411761tert-butyl 2-[(1R)-5-pyrimidin-2-yl-2,3-dihydro-1H-inden-1-yl]-2,7-diazaspiro[3.5]nonane-7-carboxylate

Product 1

HCID 674066292-[(1S)-5-Pyrimidin-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 round-bottomed flask containing tert-butyl 2-[(1R)-5-pyrimidin-2-yl-2,3-dihydro-1H-inden-1-yl]-2,7-diazaspiro[3.5]nonane-7-carboxylate (3-1d, 177 mg, 0.42 mmol) was added 5 mL of 4N HCl in dioxane. The mixture was stirred for 3 hours at room temperature and 2 mL of methanol was added to solubilize the reaction. After stirring an additional hour, the volatiles were removed under reduced pressure to give the title compound as a brown solid (190 mg, 100%). MS (APCI) 321.4 (M+H)+. 1H NMR (CD3OD) δ 2.14-2.22 (m, 5H), 2.58 (br s, 1H), 3.11 (d, 1H), 3.19-3.23 (m, 5H), 4.12 (d, 1H), 4.21 (s, 2H), 4.45-4.47 (m, 1H), 5.07-5.08 (m, 1H), 7.51 (t, 1H), 7.74 (s, 1H), 8.34-8.40 (m, 2H), 8.94 (d, 2H).

Workup

  1. customthe reaction
  2. stirringAfter stirring an additional hour
  3. customthe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-9254b13b5d2e4ad4b4b8aa1e94a7e8a4
Source dataset
uspto-grants-2013_12
Patent number
US08609680B2

Reaction notes

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