2-Pyridone → HCID 69216827, compound

HRID 272689Notes

Reaction equation

HRID 272689 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[NH:10][C:9]3[CH:13]=[C:14]([CH2:17][CH2:18][OH:19])[CH:15]=[CH:16][C:8]=3[NH:7][C:6]=2[CH:20]=1.[NH:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]1=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[NH:10][C:9]3[CH:13]=[C:14]([CH2:17][CH2:18][O:19][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][N:21]=4)[CH:15]=[CH:16][C:8]=3[NH:7][C:6]=2[CH:20]=1

Participants

6

Reactant 4

HCID 88712-PyridoneHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 69216097HCID 69216097, compound

Product 1

HCID 69216827HCID 69216827, compoundYield 37.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Example 204A (150 mg, 0.52 mmol), pyridin-2 (1H)-one (96 mg, 1.0 mmol), PPh3 (180 mg, 0.68 mmol) and di-tert-butyl azodicarboxylate (160 mg, 0.68 mmol) in 10 mL of THF was stirred overnight. The reaction mixture was purified by flash column chromatography on silica gel with 7:3 hexanes/ethyl acetate to provide 72 mg of the desired product. The column was then washed with 100:3:1 EtOAc/MeOH/NH4OH to give 79 mg of 3-chloro-8-[2-(2-oxo-2H-pyridin-1-yl)-ethyl]-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-one. MS (DCI) m/e 366 (M+H)+; 1H NMR (500 MHz, DMSO-d6) δ 9.83 (s, 1H), 8.13-8.14 (m, 1H), 7.97 (s, 1H), 7.65-7.68 (m, 2H), 7.05 (d, J=1.84 Hz, 1H), 6.89-6.95 (m, 5H), 6.76 (d, J=8.42 Hz, 1H), 4.38 (t, J=6.86 Hz, 2H), 2.99 (t, J=6.86 Hz, 2H).

Workup

  1. customThe reaction mixture was purified by flash column chromatography on silica gel with 7:3 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-568ee5f0294649de9d0856ed6c833041
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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