Tricalcium Phosphate → 3-methyl-1-(2-phenoxyphenyl)-6-(3-phenyl-1,2,4-oxadiazol-5-yl)-2H-pyrrolo[3,4-c]pyridin-4(5H)-one

HRID 2170213Notes

Reaction equation

HRID 2170213 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](O)=[O:12])[NH:8][C:7](=[O:14])[C:6]=12.C(N1C=CN=C1)(N1C=CN=C1)=O.O/[N:41]=[C:42](\[NH2:49])/[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[Ca+2].[Ca+2].[Ca+2]>CN(C)C=O>[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:12][N:49]=[C:42]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[N:41]=3)[NH:8][C:7](=[O:14])[C:6]=12

Participants

6

Reactant 4

HCID 24456Tricalcium PhosphateHCID 682631,1'-CarbonyldiimidazoleHCID 7259353613-92-3HCID 862705323-methyl-4-oxo-1-(2-phenoxyphenyl)-4,5-dihydro-2H-pyrrolo[3,4-c]pyridine-6-carboxylic acid

Product 1

HCID 1363875003-methyl-1-(2-phenoxyphenyl)-6-(3-phenyl-1,2,4-oxadiazol-5-yl)-2H-pyrrolo[3,4-c]pyridin-4(5H)-oneYield 42.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of Example 12b (500 μL, 0.005 g, 0.0139 mmol) in N,N-dimethylformamide and a solution of 1,1′-carbonyldiimidazole (500 μL, 0.0113 g, 0.069 mmol) in N,N-dimethylformamide were combined and shaken for 1 hour at ambient temperature. A solution of (Z)—N′-hydroxybenzimidamide (69.4 μL, 0.042 mmol) in N,N-dimethylformamide was added and the resulting mixture was reacted in an Anton Paar Synthos 3000 microwave optimizer at 180° C. for 45 minutes. Upon completion, the crude material was concentrated to dryness and purified by reverse phase HPLC (C8, acetonitrile/water (0.1% ammonium acetate), 25-55%) to yield 0.0027 g (37%) of the title compound as the acetic acid salt. 1H NMR (400 MHz, DMSO-d6/D2O) δ 12.39 (s, 1 H), 10.30 (s, 1 H), 8.09 (m, 2 H), 7.61 (m, 4 H), 7.54 (m, 1 H), 7.41 (m, 1 H), 7.33 (m, 3 H), 7.07 (m, 2 H), 6.95 (d, J=7.93 Hz, 2 H), 2.65 (s, 3 H). MS (ESI+) m/z 461.1 (M+H)+.

Workup

  1. concentrationUpon completion, the crude material was concentrated to dryness
  2. custompurified by reverse phase HPLC (C8, acetonitrile/water (0.1% ammonium acetate), 25-55%)

Sources & evidence

ORD record
ord-70e8b9657215402499ab98bf68d864a0
Source dataset
uspto-grants-2015_06
Patent number
US09050346B2

Reaction notes

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