Hydrochloric Acid → 4-[(R)-1-(2,7-diaza-spiro[3.5]non-2-yl)-indan-5-yl]-benzamide hydrochloride

HRID 1913459Notes

Reaction equation

HRID 1913459 reaction equation
C(OC([N:8]1[CH2:34][CH2:33][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]=[CH:28][C:27]([C:30](=[O:32])[NH2:31])=[CH:26][CH: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:35]>CCOC(C)=O.O1CCOCC1>[ClH:35].[CH2:14]1[C:11]2([CH2:10][CH2:9][NH:8][CH2:34][CH2:33]2)[CH2:12][N:13]1[C@H:15]1[C:23]2[C:18](=[CH:19][C:20]([C:24]3[CH:25]=[CH:26][C:27]([C:30]([NH2:31])=[O:32])=[CH:28][CH:29]=3)=[CH:21][CH:22]=2)[CH2:17][CH2:16]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 674077812-[(R)-5-(4-Carbamoyl-phenyl)-indan-1-yl]-2,7-diazaspiro[3.5]nonane-7-carboxylic acid tert-butyl ester

Product 1

HCID 674074174-[(R)-1-(2,7-diaza-spiro[3.5]non-2-yl)-indan-5-yl]-benzamide hydrochlorideYield 95%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-[(R)-5-(4-carbamoyl-phenyl)-indan-1-yl]-2,7-diazaspiro[3.5]nonane-7-carboxylic acid tert-butyl ester (4-1a, 124 mg, 0.27 mmol) in EtOAc (10 mL) was added 3 mL of 4N HCl in dioxane, resulting in the immediate precipitation of solids. The reaction was stirred for 3 hours. The reaction was concentrated and the residue was coevaporated with diethylether (3×) to provide 4-[(R)-1-(2,7-diaza-spiro[3.5]non-2-yl)-indan-5-yl]-benzamide hydrochloride as a white solid (102 mg, 95%). This material was used without further purification in the next reaction. MS (ES+) 362.5 (M+H)+. 1H NMR (CD3OD) δ 2.12-2.27 (m, 4H), 2.51 (dd, 1H), 2.95-3.03 (m, 1H), 3.13-3.24 (m, 4H), 3.31 (d, 3H), 4.08 (d, 1H), 4.19 (s, 2H), 4.43 (d, 1H), 5.05 (br s, 2H), 7.51-7.62 (m, 2H), 7.64-7.83 (m, 3H), 7.89-7.96 (m, 2H).

Workup

  1. customresulting in the immediate precipitation of solids
  2. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-00f00a1873964eafac159d32f5bf0942
Source dataset
uspto-grants-2013_12
Patent number
US08609680B2

Reaction notes

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