Sulfuric Acid → 4-cyano-(S)-7-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)]-1,2,3,4,6,7,8,12b-octahydro-6-oxopyrido[2,1-a][2]benzazepine

HRID 3680

Reaction equation

HRID 3680 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C@@H:12]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:13]([N:15]1[CH:20]=[CH:19][CH2:18][CH2:17][CH:16]1[C:21]#[N:22])=[O:14].S(=O)(=O)(O)O.FC(F)(F)C(OC(=O)C(F)(F)F)=O>>[C:21]([C@H:16]1[N:15]2[C:13](=[O:14])[CH:12]([N:3]3[C:4](=[O:11])[C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[C:2]3=[O:1])[CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=3[CH:20]2[CH2:19][CH2:18][CH2:17]1)#[N:22]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 9845Trifluoroacetic anhydrideHCID 15380838N-[2(S)-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-2-cyano-1,2,3,4-tetrahydro-pyridine

Product 1

HCID 698359334-cyano-(S)-7-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)]-1,2,3,4,6,7,8,12b-octahydro-6-oxopyrido[2,1-a][2]benzazepine

Procedure

Combine N-[2(S)-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-2-cyano-1,2,3,4-tetrahydro-pyridine (100 mg, 0.26 mmol), sulfuric acid (3 mL, 99.999%), and trifluoroacetic anhydride (0.03 mL). After 24 hours, the title compound is obtained as a solution.

Sources & evidence

ORD record
ord-7404f2b9601b4073b13d1d8a134a80dc
Source dataset
uspto-grants-1998_03
Patent number
US05734049

Linked notes

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