Hydrochloric Acid → 2H-benzo-furo[2,3-a]quinolizine-2-carbonitrile

HRID 1481499Notes

Reaction equation

HRID 1481499 reaction equation
Cl.Cl.C([CH:5]1[C@@H:14]2[N:9]([CH2:10][CH2:11][C:12]3[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[O:15][C:13]=32)[CH2:8][CH2:7][C@H:6]1NCCCS(N)(=O)=O)#N.[C:30](N1C=CN=C1)([N:32]1C=CN=C1)=O.Cl>>[CH:5]1[CH:6]([C:30]#[N:32])[CH:7]=[CH:8][N:9]2[C:14]=1[C:13]1[O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:12]=1[CH:11]=[CH:10]2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 121393552(2R,12bS)-[2-[(cyano-1,3,4,6,7,12b-hexahydrobenzofuro-[2,3-a]quinolizine-2-yl)-amino]-ethyl]methanesulfon-amide dihydrochloride2×

Product 1

HCID 1317366402H-benzo-furo[2,3-a]quinolizine-2-carbonitrile

Procedure

In the second step the first intermediate (2R,12bS)-[2-[(cyano-1,3,4,6,7,12b-hexahydrobenzofuro-[2,3-a]quinolizine-2-yl)-amino]-ethyl]methanesulfon-amide dihydrochloride (compound IV) reacts with 1,1′-carbonyldiimidazole in the presence of a hydrogen chloride acceptor, whereby a cyclic carbamide, the second intermediate (2R,12bS)-1,3,4,6,7,12b-hexahydro-[2,3-methylsulfonyl)-2-oxo-1-imidazolidinyl]-2H-benzo-furo[2,3-a]quinolizine-2-carbonitrile (compound V) is formed.

Sources & evidence

ORD record
ord-d4eef95cc7784989b939a265a3571282
Source dataset
uspto-grants-2016_08
Patent number
US09409919B2

Reaction notes

Loading…