Hydrochloric Acid → 2-[5-(6-Methyl-pyrimidin-4-yl)-indan-1-yl]-2,7-diaza-spiro[3.5]nonane-dihydrochloride

HRID 1913456Notes

Reaction equation

HRID 1913456 reaction equation
C(OC([N:8]1[CH2:32][CH2:31][C:11]2([CH2:14][N:13]([C@H:15]3[C:23]4[C:18](=[CH:19][C:20]([C:24]5[CH:29]=[C:28]([CH3:30])[N:27]=[CH:26][N:25]=5)=[CH:21][CH:22]=4)[CH2:17][CH2:16]3)[CH2:12]2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:33]>CO.O1CCOCC1>[ClH:33].[ClH:33].[CH3:30][C:28]1[N:27]=[CH:26][N:25]=[C:24]([C:20]2[CH:19]=[C:18]3[C:23](=[CH:22][CH:21]=2)[CH:15]([N:13]2[CH2:14][C:11]4([CH2:31][CH2:32][NH:8][CH2:9][CH2:10]4)[CH2:12]2)[CH2:16][CH2:17]3)[CH:29]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 674086712-[(R)-5-(6-Methylpyrimidin-4-yl)-indan-1-yl]-2,7-diazaspiro[3.5]nonane-7-carboxylic acid tert-butyl ester

Product 1

HCID 674060892-[5-(6-Methyl-pyrimidin-4-yl)-indan-1-yl]-2,7-diaza-spiro[3.5]nonane-dihydrochlorideYield 99.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

2-[(R)-5-(6-Methyl-pyrimidin-4-yl)-indan-1-yl]-2,7-diaza-spiro[3.5]nonane-7-carboxylic acid tert-butyl ester (3-1f, 72.6 g, 167 mmol) was suspended in methanol (363 mL) and 4M HCl in 1,4-dioxane (251 mL) was added. After stirring for 2 hours, the slurry was concentrated to dryness. The crude material was re-suspended in MeOH (500 mL) and concentrated (3×). The resulting solids were further dried under vacuum at 45° C. to afford 2-[5-(6-methyl-pyrimidin-4-yl)-indan-1-yl]-2,7-diaza-spiro[3.5]nonane-dihydrochloride (3-1g, 74.1 g, 99.9%). MS (ES+) 335.2 (M+H)+. 1H NMR (CD3OD) δ 2.16-2.23 (m, 5H), 2.59 (br s, 1H), 2.78-2.80 (m, 3H), 3.12 (br s, 1H), 3.19-3.24 (m, 4H), 3.37-3.49 (m, 1H), 4.14-4.23 (m, 3H), 4.49 (br s, 1H), 5.11 (br s, 1H), 7.84 (d, 1H), 8.30-8.34 (m, 2H), 8.46 (s, 1H), 9.36 (s, 1H).

Workup

  1. concentrationthe slurry was concentrated to dryness
  2. concentrationconcentrated (3×)
  3. customThe resulting solids were further dried under vacuum at 45° C.

Sources & evidence

ORD record
ord-2f4e7684a2654c1c8b8ac401c306464a
Source dataset
uspto-grants-2013_12
Patent number
US08609680B2

Reaction notes

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