Triethylamine → 10,11-Dihydro-10-[4-[(3-methylbutanoyl)amino]-benzoyl]-5H-pyrrolo(2,1-c][1,4]benzodiazepine

HRID 1598269Notes

Reaction equation

HRID 1598269 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][N:11]3[CH:19]=[CH:20][CH:21]=[C:10]3[CH2:9]2)=[O:7])=[CH:4][C:3]=1OC.C(N(CC)CC)C.[C:33](Cl)(=[O:38])[CH2:34][CH:35]([CH3:37])[CH3:36]>C(Cl)Cl>[CH3:36][CH:35]([CH3:37])[CH2:34][C:33]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][N:11]3[CH:19]=[CH:20][CH:21]=[C:10]3[CH2:9]2)=[O:7])=[CH:22][CH:23]=1)=[O:38]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66054Isovaleryl chlorideHCID 10806563(4-amino-3-methoxy-phenyl)[10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl]methanone

Product 1

HCID 2183706110,11-Dihydro-10-[4-[(3-methylbutanoyl)amino]-benzoyl]-5H-pyrrolo(2,1-c][1,4]benzodiazepineYield 129.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 0.10 g of 10,11-dihydro-10-(4-amino-3-methoxybenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 1 ml of methylene chloride is added 0.06 g of triethylamine followed by 0.05 g of iso-valeryl chloride. The reaction mixture is stirred for 3 hours and then quenched with 1N NaOH. The organic layer is evaporated in vacuo to a residue which is stirred in 5 ml of tetrahydrofuran for 1 hour, then evaporated in vacuo to a residue. The residue is extracted with ethyl acetate-methylene chloride, washed with brine, dried (Na2SO4), filtered through hydrous magnesium silicate and evaporated in vacuo to give 0.15 g of residue which is stirred with ether-hexane to give 0.13 g of light yellow solid. MS(CI): 418(M+H).

Workup

  1. customquenched with 1N NaOH
  2. customThe organic layer is evaporated in vacuo to a residue which
  3. stirringis stirred in 5 ml of tetrahydrofuran for 1 hour
  4. customevaporated in vacuo to a residue
  5. extractionThe residue is extracted with ethyl acetate-methylene chloride
  6. washwashed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered through hydrous magnesium silicate
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-02a52e02ace149c18ef9f71518f105b0
Source dataset
uspto-grants-1998_04
Patent number
US05736540

Reaction notes

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