m-Ethynylphenol → 5,11-Dihydro-11-ethyl-5-methyl-8-[2-(3-hydroxyphenyl)ethyl]-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

HRID 724948Notes

Reaction equation

HRID 724948 reaction equation
[CH2:1]([N:3]1[C:9]2[N:10]=[CH:11][C:12](I)=[CH:13][C:8]=2[C:7](=[O:15])[N:6]([CH3:16])[C:5]2[CH:17]=[CH:18][CH:19]=[N:20][C:4]1=2)[CH3:2].[OH:21][C:22]1[CH:23]=[C:24]([C:28]#[CH:29])[CH:25]=[CH:26][CH:27]=1>C(OCC)(=O)C.CCOCC>[CH2:1]([N:3]1[C:9]2[N:10]=[CH:11][C:12]([C:29]#[C:28][C:24]3[CH:25]=[CH:26][CH:27]=[C:22]([OH:21])[CH:23]=3)=[CH:13][C:8]=2[C:7](=[O:15])[N:6]([CH3:16])[C:5]2[CH:17]=[CH:18][CH:19]=[N:20][C:4]1=2)[CH3:2].[CH2:1]([N:3]1[C:9]2[N:10]=[CH:11][C:12]([CH2:29][CH2:28][C:24]3[CH:25]=[CH:26][CH:27]=[C:22]([OH:21])[CH:23]=3)=[CH:13][C:8]=2[C:7](=[O:15])[N:6]([CH3:16])[C:5]2[CH:17]=[CH:18][CH:19]=[N:20][C:4]1=2)[CH3:2]

Participants

5

Reactant 2

HCID 139144m-EthynylphenolHCID 10547779HCID 10547779, compound

Product 2

HCID 159563235,11-Dihydro-11-ethyl-5-methyl-8-[2-(3-hydroxyphenyl)ethyl]-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-oneHCID 197111365,11-Dihydro-11-ethyl-5-methyl-8-(3-hydroxyphenyl)ethynyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

Reagents, catalysts & solvents 1

HCID 21584169Diethylether ethylacetateSolvent

Procedure

5,11-Dihydro-11-ethyl-5-methyl-8-(3-hydroxyphenyl)ethynyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.10 g) was prepared by coupling 5,11-dihydro-11-ethyl-8-iodo-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one with 3-hydroxyphenylacetylene by a procedure analogous to that described in Example 42a. Hydrogenation as described in Example 42b afforded 7 mg of the title compound, m.p. 177°-179° C. (ethyl acetate/ether).

Sources & evidence

ORD record
ord-26f2bcfac740487aa27a0c3054b5b599
Source dataset
uspto-grants-1998_01
Patent number
US05705499

Reaction notes

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