Trifluoroacetic acid → 2-Amino-5,11-dihydro-11-ethyl-8-[2-(4-pyridyl)ethyl]-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

HRID 724927Notes

Reaction equation

HRID 724927 reaction equation
COC1C=CC(C[NH:8][C:9]2[CH:10]=[CH:11][C:12]3[N:13]([CH3:35])[C:14](=[O:34])[C:15]4[CH:25]=[C:24]([CH2:26][CH2:27][C:28]5[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=5)[CH:23]=[N:22][C:16]=4[N:17]([CH2:20][CH3:21])[C:18]=3[N:19]=2)=CC=1.FC(F)(F)C(O)=O>>[NH2:8][C:9]1[CH:10]=[CH:11][C:12]2[N:13]([CH3:35])[C:14](=[O:34])[C:15]3[CH:25]=[C:24]([CH2:26][CH2:27][C:28]4[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=4)[CH:23]=[N:22][C:16]=3[N:17]([CH2:20][CH3:21])[C:18]=2[N:19]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 197111072-(4-methoxybenzylamino)-5,11-dihydro-11-ethyl-8-[2-(4-pyridyl)ethyl]-5-methyl-6-H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

Product 1

HCID 159562982-Amino-5,11-dihydro-11-ethyl-8-[2-(4-pyridyl)ethyl]-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-oneYield 71.2%

Procedure

2-(4-methoxybenzylamino)-5,11-dihydro-11-ethyl-8-[2-(4-pyridyl)ethyl]-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.09 g, 0.18 mmol) was treated for 20 h with trifluoroacetic acid (1 mL) under argon. After removal of excess TFA, the residue was stirred in dilute ammonium hydroxide for 5 hours. The product was extracted with ethyl acetate and purified by flash chromatography (elution with methanol-dichloromethane) to give the title compound (48 mg, 71%), m.p. 94°-97° C.

Workup

  1. customAfter removal of excess TFA
  2. extractionThe product was extracted with ethyl acetate
  3. custompurified by flash chromatography (elution with methanol-dichloromethane)

Sources & evidence

ORD record
ord-59bc9a094e484035a6a983545dafd0af
Source dataset
uspto-grants-1998_01
Patent number
US05705499

Reaction notes

Loading…