HCID 12671370, compound → HCID 89614825, compound

HRID 1747752Notes

Reaction equation

HRID 1747752 reaction equation
[C:1]1([C:7]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15]3[CH:14]=[CH:13][N:12]=[CH:11][C:10]=3[C:9](=[O:16])[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C2(C3C=CC=CC=3)C3CNCCC=3C(=O)O2)C=CC=CC=1>>[C:17]1([C:7]2([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:15]3[CH2:14][CH2:13][NH:12][CH2:11][C:10]=3[C:9](=[O:16])[O:8]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 12671370HCID 12671370, compoundHCID 117901131HCID 117901131, compound2×

Product 1

HCID 89614825HCID 89614825, compound

Procedure

The title compound was synthesized in a manner analogous to R06039-222 except 3-diisopropylamidopyridine was coupled to benzophenone to provide intermediate 1,1-diphenylfuro[3,4-c]pyridin-3-one. 1,1-diphenylfuro[3,4-c]pyridin-3-one was reduced in a manner analogous to 3,3-diphenyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-1(3H)-one (compound 2) to afford 1,1-diphenyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-3-one. Benzyl isocyanate (0.023 g, 0.17 mmol) was then added to a solution of 1,1-diphenyl-4,5,6,7-tetrahydrofuro[3,4-c]pyridin-3-one (0.05 g, 0.17 mmol) in dichloromethane (10 mL) and was stirred at room temperature for 1 h. The solvent was removed and the resulting residue was purified on silica to give the desired product (0.038 g, 50%). 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 3.66-3.70 (dd, 2H, J=6 Hz), 4.10-4.15 (m, 2H), 4.34-4.42 (dd, 2H, J=6 Hz), 5.09 (t, 1H, J=6 Hz), 7.20-7.38 (m, 15H).

Sources & evidence

ORD record
ord-6559286df3a74dcab767d747c7d6e676
Source dataset
uspto-grants-2015_10
Patent number
US09150582B2

Reaction notes

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