Formic Acid → HCID 70000117, compound

HRID 1634043Notes

Reaction equation

HRID 1634043 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][N:6]1[C:12](=[O:13])[C:11]2[CH:14]=[C:15]([N+:18]([O-])=O)[CH:16]=[CH:17][C:10]=2[N:9]([CH3:21])[C:8](=[O:22])[CH2:7]1)[CH3:2].C(N(CC)CC)C.C(O)=O>CC#N.[Pd]>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][N:6]1[C:12](=[O:13])[C:11]2[CH:14]=[C:15]([NH2:18])[CH:16]=[CH:17][C:10]=2[N:9]([CH3:21])[C:8](=[O:22])[CH2:7]1)[CH3:2]

Participants

6

Reactant 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 69998297HCID 69998297, compound

Product 1

HCID 70000117HCID 70000117, compoundYield 65.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
5 °C

Procedure

To a solution of (1-methyl-7-nitro-2,5-dioxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-acetic acid ethyl ester (3.21 g, 10 mmol) in MeCN(15 ml) was added triethylamine (5.85 ml, 42.5 mmol). After cooling of this mixture to about 5° C. Pd—C (10%, 200 mg) and a solution of formic acid (1.6 ml) in MeCN(2 ml) were added. The ice bath was removed, gas evolution started and the temperature of the reaction mixture rose to 35° C. After 1 h the reaction mixture was heated to reflux temperature until all starting material had disappeared according to TLC. After filtration, evaporation of the solvents, and chromatography (silica gel, dichloromethane/MeOH 19:1) (7-amino-1-methyl-2,5-dioxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-acetic acid ethyl ester (1.9 g) was isolated: mp. 118-119° C.; MS (EI): 291 (M)+.

Workup

  1. customThe ice bath was removed
  2. customrose to 35° C
  3. temperatureAfter 1 h the reaction mixture was heated
  4. temperatureto reflux temperature until all starting material
  5. filtrationAfter filtration, evaporation of the solvents

Sources & evidence

ORD record
ord-f10422402d7c4b9ab6d6966141a7cae0
Source dataset
uspto-grants-2003_01
Patent number
US06506744B1

Reaction notes

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