HCID 68313150, compound → HCID 68313054, compound

HRID 1530527Notes

Reaction equation

HRID 1530527 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([CH:17]([O:19][C:20]2[CH:41]=[CH:40][C:23]3[C:24]4[N:28]([CH2:29][CH2:30][O:31][C:22]=3[CH:21]=2)[CH:27]=[C:26]([C:32]2[N:33]([CH:37]([CH3:39])[CH3:38])[N:34]=[CH:35][N:36]=2)[N:25]=4)[CH3:18])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>CCOC(C)=O.[Pd]>[CH:37]([N:33]1[C:32]([C:26]2[N:25]=[C:24]3[N:28]([CH2:29][CH2:30][O:31][C:22]4[CH:21]=[C:20]([O:19][CH:17]([CH:14]5[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]5)[CH3:18])[CH:41]=[CH:40][C:23]=43)[CH:27]=2)=[N:36][CH:35]=[N:34]1)([CH3:38])[CH3:39]

Participants

4

Reactant 1

HCID 68313150HCID 68313150, compound

Product 1

HCID 68313054HCID 68313054, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 4-{1-[2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-8-yloxy]ethyl}piperidine-1-carboxylic acid benzyl ester (278 mg, 0.50 mmol) and 10% Pd/C (150 mg) in EtOAc (10 mL) was stirred under an atmosphere of H2 at RT for 1 h then heated at 50° C. for 3 h. The reaction mixture was filtered through Celite® and the filtrate concentrated in vacuo to afford 2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-8-(1-piperidin-4-ylethoxy)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene (211 mg, quantitative) as a colourless oil. LCMS: RT 2.26 min [M+H]+ 423.4

Workup

  1. temperaturethen heated at 50° C. for 3 h
  2. filtrationThe reaction mixture was filtered through Celite®
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-ddc575adfdf14a7db946bbf87f6ee7eb
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

Loading…