Hydrochloric Acid → Isoindolin-5-yl(9-(pyridin-4-yl)-3,9-diazaspiro[5.5]undecan-3-yl)methanone

HRID 1808380Notes

Reaction equation

HRID 1808380 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:36][CH2:35][C:11]3([CH2:16][CH2:15][N:14]([C:17]([C:19]4[CH:20]=[C:21]5[C:25](=[CH:26][CH:27]=4)[CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22]5)=[O:18])[CH2:13][CH2:12]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1>CO>[CH2:24]1[C:25]2[C:21](=[CH:20][C:19]([C:17]([N:14]3[CH2:13][CH2:12][C:11]4([CH2:35][CH2:36][N:8]([C:5]5[CH:6]=[CH:7][N:2]=[CH:3][CH:4]=5)[CH2:9][CH2:10]4)[CH2:16][CH2:15]3)=[O:18])=[CH:27][CH:26]=2)[CH2:22][NH:23]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59483841tert-Butyl 5-(9-(pyridin-4-yl)-3,9-diazaspiro[5.5]undecane-3-carbonyl)isoindoline-2-carboxylate

Product 1

HCID 59483811Isoindolin-5-yl(9-(pyridin-4-yl)-3,9-diazaspiro[5.5]undecan-3-yl)methanone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1.25 M hydrogen chloride in methanol (7.1 ml, 8.92 mmol) was added at RT to a solution of tert-butyl 5-(9-(pyridin-4-yl)-3,9-diazaspiro[5.5]undecane-3-carbonyl)isoindoline-2-carboxylate (0.85 g, 1.78 mmol) in methanol (1 ml), and the reaction mixture was refluxed for 1 h. The solvent was removed in vacuo, the residue was taken up in a small amount of ethanol (2 ml), and diethyl ether (50 ml) was added. The mixture was then cooled for 30 min in an ice bath, and the resulting solid was filtered out, washed with diethyl ether and dried in vacuo. Yield: 0.74 g (92%).

Workup

  1. temperaturethe reaction mixture was refluxed for 1 h
  2. customThe solvent was removed in vacuo
  3. additionwas added
  4. temperatureThe mixture was then cooled for 30 min in an ice bath
  5. filtrationthe resulting solid was filtered out
  6. washwashed with diethyl ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-ce308bd8500444c68b5fc3a12e04cec2
Source dataset
uspto-grants-2013_01
Patent number
US08357717B2

Reaction notes

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