Hydrochloric Acid → 5-[(R)-1-(2,7-Diaza-spiro[3.5]non-2-yl)-indan-5-yl]-pyrazine-2-carboxylic acid amide dihydrochloride

HRID 1913469Notes

Reaction equation

HRID 1913469 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]=[N:28][C:27]([C:30](=[O:32])[NH2:31])=[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: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[N:25]=[CH:26][C:27]([C:30]([NH2:31])=[O:32])=[N:28][CH:29]=3)=[CH:21][CH:22]=2)[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 674113452-[(R)-5-(5-Carbamoyl-pyrazin-2-yl)-indan-1-yl]-2,7-diaza-spiro[3.5]nonane-7-carboxylic acid tert-butyl ester

Product 1

HCID 866577265-[(R)-1-(2,7-Diaza-spiro[3.5]non-2-yl)-indan-5-yl]-pyrazine-2-carboxylic acid amide dihydrochlorideYield 45%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 2-[(R)-5-(5-carbamoyl-pyrazin-2-yl)-indan-1-yl]-2,7-diaza-spiro[3.5]nonane-7-carboxylic acid tert-butyl ester (10-1b, 150 mg, 0.32 mmol) was added 5 mL of 4N HCl in dioxane. The mixture was stirred for 3 hours. The volatiles were removed under reduced pressure to give the title compound as a brown solid (65 mg, 45%). MS (APCI) 364.2 (M+H)+. 1H NMR (CD3OD) δ 2.20-2.24 (m, 4H), 2.63 (s, 1H), 3.15 (d, 4H), 3.29-3.38 (m, 3H), 4.25 (s, 3H), 4.48 (s, 1H), 5.10 (br s, 1H), 7.79 (d, 1H), 8.18 (d, 1H), 8.24 (s, 1H), 9.22 (s, 1H), 9.30 (s, 1H).

Workup

  1. customThe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-a493f783f37f45d6a9206d41022120c1
Source dataset
uspto-grants-2013_12
Patent number
US08609680B2

Reaction notes

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