Hydrochloric Acid → HCID 67406275, compound

HRID 1913466Notes

Reaction equation

HRID 1913466 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:25]=[N:26][C:27]([C:30](=[O:32])[NH2:31])=[CH:28][CH:29]=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]>O1CCOCC1>[ClH:35].[ClH:35].[CH2:12]1[C:11]2([CH2:33][CH2:34][NH:8][CH2:9][CH2:10]2)[CH2:14][N:13]1[C@H:15]1[C:23]2[C:18](=[CH:19][C:20]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([NH2:31])=[O:32])=[N:26][CH:25]=3)=[CH:21][CH:22]=2)[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67410299HCID 67410299, compound

Product 1

HCID 67406275HCID 67406275, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a mixture of 2-[(R)-5-(6-carbamoyl-pyridin-3-yl)-indan-1-yl]-2,7-diaza-spiro[3.5]nonane-7-carboxylic acid tert-butyl ester (9-1a, 440 mg, 0.95 mmol) in 1,4-dioxane (10 mL) was added 5 mL of 4N HCl in dioxane. This resulted 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×) until 5-[(R)-1-(2,7-diaza-spiro[3.5]non-2-yl)-indan-5-yl]-pyridine-2-carboxylic acid amide dihydrochloride (9-1b, 414 mg, 100%) was obtained as a white solid. This material was used without further purification in the next reaction. MS (ES+) 363.1 (M+H)+. 1H NMR (CD3OD) δ 2.22-2.26 (m, 5H), 2.56-2.66 (m, 1H), 3.19-3.22 (m, 4H), 3.35 (s, 1H), 3.63-3.66 (m, 1H), 4.15 (d, 1H), 4.24 (s, 2H), 4.47 (s, 1H), 5.09 (br s, 1H), 7.85 (s, 1H), 7.81 (s, 2H), 8.29-8.31 (m, 3H), 8.45 (br s, 1H), 9.07 (br s, 1H).

Workup

  1. customThis resulted in the immediate precipitation of solids
  2. concentrationThe reaction was concentrated
  3. customwas obtained as a white solid
  4. customThis material was used without further purification in the next reaction

Sources & evidence

ORD record
ord-ebd671a717794a01a42e8047635afb30
Source dataset
uspto-grants-2013_12
Patent number
US08609680B2

Reaction notes

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