Hydrochloric Acid → 2-((R)-5-(4-methyl-1H-pyrazol-1-yl)-2,3-dihydro-1H-inden-1-yl)-2,7-diazaspiro[3.5]nonane dihydrochloride

HRID 1913464Notes

Reaction equation

HRID 1913464 reaction equation
C(OC([N:8]1[CH2:31][CH2:30][C:11]2([CH2:14][N:13]([C@H:15]3[C:23]4[C:18](=[CH:19][C:20]([N:24]5[CH:28]=[C:27]([CH3:29])[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:32]>CO.O1CCOCC1>[ClH:32].[ClH:32].[CH3:29][C:27]1[CH:26]=[N:25][N:24]([C:20]2[CH:19]=[C:18]3[C:23](=[CH:22][CH:21]=2)[C@H:15]([N:13]2[CH2:14][C:11]4([CH2:30][CH2:31][NH:8][CH2:9][CH2:10]4)[CH2:12]2)[CH2:16][CH2:17]3)[CH:28]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 674102302-[(R)-5-(4-methyl-pyrazol-1-yl)-indan-1-yl]-2,7-diaza-spiro[3.5]nonane-7-carboxylic acid tert-butyl ester

Product 1

HCID 674053182-((R)-5-(4-methyl-1H-pyrazol-1-yl)-2,3-dihydro-1H-inden-1-yl)-2,7-diazaspiro[3.5]nonane dihydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-[(R)-5-(4-methyl-pyrazol-1-yl)-indan-1-yl]-2,7-diaza-spiro[3.5]nonane-7-carboxylic acid tert-butyl ester (8-1a, 239 mg, 0.57 mmol) in MeOH (5 mL) was added 9 mL of 4N HCl in dioxane solution. The reaction was stirred for 3 hours. The reaction was concentrated and the residue was coevaporated with diethylether (3×) to afford 2-((R)-5-(4-methyl-1H-pyrazol-1-yl)-2,3-dihydro-1H-inden-1-yl)-2,7-diazaspiro[3.5]nonane dihydrochloride as a white solid (8-1b, 135 mg, 61%). This material was used without further purification in the next reaction. MS (ES+) 322.9 (M+H)+. 1H NMR (DMSO-d6) δ 1.89-2.20 (m, 7H), 2.28-2.48 (m, 2H), 2.84-3.14 (m, 4H), 3.28-3.46 (m, 1H), 3.84-4.03 (m, 3H), 4.19-4.33 (m, 2H), 4.83-4.98 (m, 1H), 7.54 (s, 1H), 7.66 (s, 2H), 7.74-7.79 (m, 1H), 8.28 (s, 1H).

Workup

  1. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-4e3b7b3865e549a49a8cbf9170998c86
Source dataset
uspto-grants-2013_12
Patent number
US08609680B2

Reaction notes

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