1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-methyl-1-(2-phenoxyphenyl)-6-(3-(pyridin-3-yl)-1,2,4-oxadiazol-5-yl)-2H-pyrrolo[3,4-c]pyridin-4(5H)-one

HRID 2170215Notes

Reaction equation

HRID 2170215 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:5]2[CH:10]=[C:9]([C:11]([OH:13])=O)[NH:8][C:7](=[O:14])[C:6]=12.C(N=C=NCCCN(C)C)C.O/[N:40]=[C:41](\[NH2:48])/[C:42]1[CH:47]=[CH:46][CH:45]=[N:44][CH:43]=1>CN(C)C=O.N1C=CC=CC=1>[CH3:1][C:2]1[NH:3][C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:5]2[CH:10]=[C:9]([C:11]3[O:13][N:48]=[C:41]([C:42]4[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=4)[N:40]=3)[NH:8][C:7](=[O:14])[C:6]=12

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 53723343-Pyridinecarboxamide OximeHCID 862705323-methyl-4-oxo-1-(2-phenoxyphenyl)-4,5-dihydro-2H-pyrrolo[3,4-c]pyridine-6-carboxylic acid

Product 1

HCID 1363875153-methyl-1-(2-phenoxyphenyl)-6-(3-(pyridin-3-yl)-1,2,4-oxadiazol-5-yl)-2H-pyrrolo[3,4-c]pyridin-4(5H)-oneYield 9%

Reagents, catalysts & solvents 1

HCID 21954950Dimethylformamide pyridineSolvent3×

Procedure

A solution of Example 12b (200 μL, 0.0275 g, 0.076 mmol) in N,N-dimethylformamide/pyridine (1:1 v/v), a solution of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (200 μL, 0.0225 g, 0.145 mmol) in N,N-dimethylformamide/pyridine (1:1 v/v), and a solution of (Z)—N′-hydroxynicotinimidamide (173.0 μL, 0.103 mmol) in 1 mL of N,N-dimethylformamide/pyridine (1:1 v/v) were combined and shaken at ambient temperature overnight. Upon completion, the reaction mixture was concentrated to dryness. The residue was purified by reverse phase HPLC (C8, acetonitrile/water (0.1% ammonium acetate), 45-75%) to give 0.0031 g (9%) of the title compound. 1H NMR (400 MHz, DMSO-d6/D2O) δ 9.24 (dd, J=2.14, 0.61 Hz, 1H), 8.81 (dd, J=4.88, 1.83 Hz, 1 H), 8.45 (ddd, J=8.09, 1.83, 1.68 Hz, 1 H), 7.67 (m, 1 H), 7.64 (dd, J=7.63, 1.83 Hz, 1 H), 7.59 (s, 1 H), 7.44 (m, 1 H), 7.34 (m, 3 H), 7.07 (m, 2 H), 6.95 (m, 2 H), 2.66 (s, 3 H). MS (ESI+) m/z 562.0 (M+H)+.

Workup

  1. concentrationUpon completion, the reaction mixture was concentrated to dryness
  2. customThe residue was purified by reverse phase HPLC (C8, acetonitrile/water (0.1% ammonium acetate), 45-75%)

Sources & evidence

ORD record
ord-6d1d472d88334ea59dcc7ccbc7262d6b
Source dataset
uspto-grants-2015_06
Patent number
US09050346B2

Reaction notes

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