Triethylamine → HCID 54481943, compound

HRID 979618Notes

Reaction equation

HRID 979618 reaction equation
[C:1]1([C:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]([CH2:18][CH2:19][CH2:20][NH2:21])[C:10]3[N:22]=[CH:23][CH:24]=[CH:25][C:9]=3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl[C:34]([O:36][CH2:37][CH3:38])=[O:35]>C(Cl)Cl>[CH2:37]([O:36][C:34](=[O:35])[NH:21][CH2:20][CH2:19][CH2:18][N:11]1[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8][C:9]2[CH:25]=[CH:24][CH:23]=[N:22][C:10]1=2)[CH3:38]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 15586690HCID 15586690, compound

Product 1

HCID 54481943HCID 54481943, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.6 g (0.0045 mole) of 6-phenyl-11H-pyrido[2,3-b][1,4]benzodiazepine-11-propanamine in dry methylene chloride was added 0.53 g (0.0052 mole) of triethylamine. To this solution was added dropwise, while cooling, 0.54 g (0.0050 mole) of ethyl chloroformate. The mixture was stirred at room temperature for 2 hr. The methylene chloride solution of the product (as indicated by chemical ionization mass spec) was washed with dilute sodium hydroxide-sodium chloride saturated aqueous solution and dried and concentrated to dryness. The residue was triturated in isopropyl ether. Yield was 1.5 g of title product.

Workup

  1. additionTo this solution was added dropwise
  2. temperaturewhile cooling
  3. washThe methylene chloride solution of the product (as indicated by chemical ionization mass spec) was washed with dilute sodium hydroxide-sodium chloride saturated aqueous solution
  4. customdried
  5. concentrationconcentrated to dryness
  6. customThe residue was triturated in isopropyl ether

Sources & evidence

ORD record
ord-e7fed926d46040fc96935c0bbb61a45e
Source dataset
uspto-grants-1987_05
Patent number
US04668675

Reaction notes

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