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

HRID 724976Notes

Reaction equation

HRID 724976 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)O.CC(C)([O-])C.[K+].[Cl:15][C:16]1[CH:17]=[CH:18][C:19]2[N:20]([CH3:36])[C:21](=[O:35])[C:22]3[CH:32]=[C:31]([CH2:33]Cl)[CH:30]=[N:29][C:23]=3[N:24]([CH2:27][CH3:28])[C:25]=2[N:26]=1>CS(C)=O.C(OCC)(=O)C>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]2[N:20]([CH3:36])[C:21](=[O:35])[C:22]3[CH:32]=[C:31]([CH2:33][C:1]4[CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=4)[CH:30]=[N:29][C:23]=3[N:24]([CH2:27][CH3:28])[C:25]=2[N:26]=1

Participants

6

Reactant 3

HCID 5054ResorcinolHCID 108307382-chloro-8-chloromethyl-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 159563382-chloro-5,11-dihydro-11-ethyl-8-(3-hydroxyphenyl)methyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-oneYield 56.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Resorcinol (0.082 g, 0.74 mmol) in dimethyl sulfoxide (1 mL) was treated with potassium tert-butoxide (1.0M in tetrahydrofuran, 0.15 mL, 0.15 mmol). The resulting stirred solution was treated with 2-chloro-8-chloromethyl-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.050 g, 0.14 mmol) in dimethyl sulfoxide (1 mL) and the mixture was stirred an additional 16 hours. The mixture was diluted with ethyl acetate (50 mL) washed with brine, water, and brine (15 mL each). The organics were dried over sodium sulfate, concentrated and the residue was purified by flash chromatography (hexanes to 1:1 hexanes/ethyl acetate gradient) followed by crystallization from hexanes to give the title compound (0.031 g, 51%), m.p. 219°-220° C.

Workup

  1. stirringthe mixture was stirred an additional 16 hours
  2. washwashed with brine, water, and brine (15 mL each)
  3. dry with materialThe organics were dried over sodium sulfate
  4. concentrationconcentrated
  5. customthe residue was purified by flash chromatography (hexanes to 1:1 hexanes/ethyl acetate gradient)
  6. customfollowed by crystallization from hexanes

Sources & evidence

ORD record
ord-7cd25f6d86a145dc94cc7ac0bae4962f
Source dataset
uspto-grants-1998_01
Patent number
US05705499

Reaction notes

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