Hydrochloric Acid → HCID 67050777, compound

HRID 1629400Notes

Reaction equation

HRID 1629400 reaction equation
C(OC([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:36]=[CH:35][C:17]3[C:18]4[N:22]([CH2:23][CH2:24][O:25][C:16]=3[CH:15]=2)[CH:21]=[C:20]([C:26](=[O:34])[N:27]([CH2:31][CH2:32][OH:33])[CH:28]([CH3:30])[CH3:29])[N:19]=4)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:37]>[Pd]>[ClH:37].[OH:33][CH2:32][CH2:31][N:27]([CH:28]([CH3:30])[CH3:29])[C:26]([C:20]1[N:19]=[C:18]2[N:22]([CH2:23][CH2:24][O:25][C:16]3[CH:15]=[C:14]([CH:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)[CH:36]=[CH:35][C:17]=32)[CH:21]=1)=[O:34]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58204357HCID 58204357, compound

Product 1

HCID 67050777HCID 67050777, compoundYield 110%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
50 °C

Procedure

To a solution of 4-{2-[(2-hydroxy-ethyl)-isopropyl-carbamoyl]-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulen-8-yl}-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (112 mg, 0.23 mmol) in IMS (3 mL) was added hydrochloric acid (2 mL, 2M, 4.0 mmol) and palladium on carbon (20 mg, 10% by wt) added. The reaction mixture was stirred under an atmosphere of hydrogen at 50° C. for 4.5 h. The reaction mixture was filtered and the solids washed with IMS (10 mL). The filtrate was concentrated in vacuo and azeotroped with acetonitrile to yield 8-piperidin-4-yl-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene-2-carboxylic acid (2-hydroxy-ethyl)-isopropyl-amide hydrochloride as a thick oil (110 mg). LCMS: RT=0.32 min, [M+H]+=399

Workup

  1. additionadded
  2. filtrationThe reaction mixture was filtered
  3. washthe solids washed with IMS (10 mL)
  4. concentrationThe filtrate was concentrated in vacuo
  5. customazeotroped with acetonitrile

Sources & evidence

ORD record
ord-1d1e3996656842fdb25e87906d898a58
Source dataset
uspto-grants-2014_07
Patent number
US08785626B2

Reaction notes

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