Ammonium formate → HCID 20762210, compound

HRID 982885Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]([C:10]1[C:19]2[C:18](=[O:20])[CH:17]3[CH2:21][N:22](CC4C=CC=CC=4)[CH2:23][CH:16]3[CH2:15][CH2:14][C:13]=2[NH:12][CH:11]=1)=[O:9].C([O-])=O.[NH4+]>CCO.[OH-].[OH-].[Pd+2]>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]([C:10]1[C:19]2[C:18](=[O:20])[CH:17]3[CH2:21][NH:22][CH2:23][CH:16]3[CH2:15][CH2:14][C:13]=2[NH:12][CH:11]=1)=[O:9]

Participants

Conditions

Temperature: 78 °C

Procedure

Pd(OH)2 (Pearlman's catalyst, 30 mg) is added to a solution of 6-benzyl-4-oxo-4,4a,5,6,7,7a,8,9-octahydro-1H-1,6-diaza-cyclopenta[f]azulene-3-carboxylic acid pyridin-2-ylamide (65 mg, 0.16 mmol) and HCOONH4 (204 mg, 3.24 mmol) in EtOH (10 ml). The reaction mixture is heated at 78° C. for 20 min. Pd catalyst is filtered off with celite. The solvent is removed by rotavapor. The residue is loaded on a column (0.5% TEA+19.5% MeOH+80% CH3CN) to provide the title compound (20 mg, 40%) as white solid. This compound may be salted as HCl salt. 1H NMR (400 MHz, CD3OD) δ 1.98 (1H, m), 2.01-2.16 (2H, m), 2.65 (1H, m), 3.02-3.25 (5H, m), 3.76 (1H, m), 7.09 (1H, m), 7.57 (1H, s), 7.78 (1H, m), 8.27 (2H, m). MS (ES+) 311 (M+1)

Workup

filtrationPd catalyst is filtered off with celite
customThe solvent is removed by rotavapor

Sources & evidence

ORD record: ord-19241ea3d5ed4611b057bf96af8eba99
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06861529B2

Reaction notes

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