Citric Acid → 12-amino-3-fluoro-6H-[1]benzothieno[2,3-b][1,5]benzodiazepine

HRID 649955Notes

Reaction equation

HRID 649955 reaction equation
[NH2:1][C:2]1[C:3]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[S:14][C:4]=2[NH:5][C:6]2[CH:12]=[C:11](F)[CH:10]=[CH:9][C:7]=2[N:8]=1.Cl.CN(C)CCNC.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[F:42]C1C=CC2N=C(N(CCN(C)C)C)C3C4C=CC=CC=4SC=3NC=2C=1>CS(C)=O>[NH2:1][C:2]1[C:3]2[C:16]3[CH:17]=[CH:18][C:19]([F:42])=[CH:20][C:15]=3[S:14][C:4]=2[NH:5][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=1

Participants

7

Reactant 5

HCID 311Citric AcidHCID 313Hydrochloric AcidHCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 1842238512-amino-8-fluoro-6H-[1]benzothieno[2,3-b][1,5]benzodiazepineHCID 217135918-fluoro-12-[N-(2-dimethylaminoethyl)-N-methylamino]-6H-[1]benzothieno[2,3-b][1,5]benzodiazepine

Product 1

HCID 13581640212-amino-3-fluoro-6H-[1]benzothieno[2,3-b][1,5]benzodiazepine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In the same manner as in Example 42 and using 12-amino-8-fluoro-6H-[1]benzothieno[2,3-b][1,5]benzodiazepine.1 hydrochloride (1.3 g), N,N,N′-trimethylethylenediamine (13 g), dimethyl sulfoxide (5 ml) and citric acid, 8-fluoro-12-[N-(2-dimethylaminoethyl)-N-methylamino]-6H-[1]benzothieno[2,3-b][1,5]benzodiazepine.1 citrate 1 hydrate (289 mg) was obtained.

Sources & evidence

ORD record
ord-7084f4f0d05f4a87880fa8d69e3129bd
Source dataset
uspto-grants-2001_08
Patent number
US06271225B1

Reaction notes

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