(+-)-Anabasine → HCID 178463464, compound

HRID 34209Notes

Reaction equation

HRID 34209 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12](O)=[O:13])[N:8]=[CH:7][N:6]=[C:5]2[NH:15][CH:16]([C:18]1[NH:22][C:21]2[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:20]=2[N:19]=1)[CH3:17].FC1C(OC(N(C)C)=[N+](C)C)=C(F)C(F)=C(F)C=1F.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[N:63]1[CH:68]=[CH:67][CH:66]=[C:65]([CH:69]2[CH2:74][CH2:73][CH2:72][CH2:71][NH:70]2)[CH:64]=1>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12]([N:70]1[CH2:71][CH2:72][CH2:73][CH2:74][CH:69]1[C:65]1[CH:64]=[N:63][CH:68]=[CH:67][CH:66]=1)=[O:13])[N:8]=[CH:7][N:6]=[C:5]2[NH:15][CH:16]([C:18]1[NH:22][C:21]2[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:20]=2[N:19]=1)[CH3:17]

Participants

6

Reactant 4

HCID 2181(+-)-AnabasineHCID 81531DiisopropylethylamineHCID 15840204Pentafluorphenol-tetramethyluronium hexafluorophosphatHCID 1784635046-chloro-4-(1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-hydroxycarbonyl-quinazoline

Product 1

HCID 178463464HCID 178463464, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Prepared analogously to Example 37a from 6-chloro-4-[1-(5-chloro-1H-benzimidazol-2-yl)-ethylamino]-7-hydroxycarbonyl-quinazoline, pentafluorophenyl-tetramethyluronium-hexafluorophosphate (PFTU), diisopropylethylamine and 2-(pyridin-3-yl)-piperidine in DMSO at ambient temperature.

Sources & evidence

ORD record
ord-00329d608b2442d3b6533b7485d61d9e
Source dataset
uspto-grants-2008_09
Patent number
US07429597B2

Reaction notes

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