5,10-Dihydro-11H-dibenzo(b,e)(1,4)diazepin-11-one → 5,10-dihydro-5-[(1,5-dimethyl-1,2,5,6-tetrahydro-4-pyridinyl)-carbonyl]-11H-dibenzo[b,e][1,4]diazepin-11-one

HRID 543715

Reaction equation

HRID 543715 reaction equation
[CH:1]1C2C(=O)NC3C=CC=CC=3NC=2C=CC=1.CC1C=NC=CC=1C(Cl)=O.C1C2C(=O)N=C3C=CC=CC3=NC=2C=CC=1.C(OC(C)C)(C)C.CO.[CH3:52][C:53]1[CH:54]=[N:55][CH:56]=[CH:57][C:58]=1[C:59]([N:61]1[C:67]2[CH:68]=[CH:69][CH:70]=[CH:71][C:66]=2[C:65](=[O:72])[NH:64][C:63]2[CH:73]=[CH:74][CH:75]=[CH:76][C:62]1=2)=[O:60]>>[CH3:1][N:55]1[CH2:54][CH:53]([CH3:52])[C:58]([C:59]([N:61]2[C:67]3[CH:68]=[CH:69][CH:70]=[CH:71][C:66]=3[C:65](=[O:72])[NH:64][C:63]3[CH:73]=[CH:74][CH:75]=[CH:76][C:62]2=3)=[O:60])=[CH:57][CH2:56]1

Participants

6

Reactant 5

HCID 2013275,10-Dihydro-11H-dibenzo(b,e)(1,4)diazepin-11-oneHCID 132858635,10-dihydro-5[(3-methyl-4-pyridinyl)carbonyl]-11H-dibenzo[b,e][1,4]-diazepin-11-oneHCID 132858643-Methylpyridine-4-carbonyl chlorideHCID 19781529Benzo[b][1,4]benzodiazepin-6-oneHCID 21882575Diisopropylether methanol

Product 1

HCID 204604705,10-dihydro-5-[(1,5-dimethyl-1,2,5,6-tetrahydro-4-pyridinyl)-carbonyl]-11H-dibenzo[b,e][1,4]diazepin-11-one

Procedure

By reacting 5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one with 3-methylisonicotinic acid chloride (m.p. 155°-156° C.) via 5,10-dihydro-5-[3-methyl-4-pyridinyl)carbonyl]-11H-dibenzo[b,e][1,4]diazepin-11-one, m.p. 223°-224° C. (diisopropylether/methanol) and 5,10-dihydro-5[(3-methyl-4-pyridinyl)carbonyl]-11H-dibenzo[b,e][1,4]-diazepin-11-one methoiodide;

Sources & evidence

ORD record
ord-ed1696b1d7f04771a91568d987f79a12
Source dataset
uspto-grants-1984_05
Patent number
US04447434

Linked notes

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