Acetic Acid → HCID 70656505, compound

HRID 68966Notes

Reaction equation

HRID 68966 reaction equation
[CH2:1]([N:3]1[C:9](=[O:10])[C:8]([CH3:12])([CH3:11])[C:7](=[O:13])[N:6]([CH3:14])[C:5]2[CH:15]=[C:16]([CH:19]=O)[CH:17]=[CH:18][C:4]1=2)[CH3:2].C(O)(=O)C.[CH3:25][C:26]1[N:27]=[CH:28][S:29][C:30]=1[CH2:31][NH:32][CH2:33][CH2:34][C:35]1[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:1]([N:3]1[C:9](=[O:10])[C:8]([CH3:12])([CH3:11])[C:7](=[O:13])[N:6]([CH3:14])[C:5]2[CH:15]=[C:16]([CH2:19][N:32]([CH2:31][C:30]3[S:29][CH:28]=[N:27][C:26]=3[CH3:25])[CH2:33][CH2:34][C:35]3[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=3)[CH:17]=[CH:18][C:4]1=2)[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 65721669N-(4-methylthiazol-5-ylmethyl)-N-(2-pyridin-3-ylethyl)amineHCID 866704761-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine-7-carbaldehyde

Product 1

HCID 70656505HCID 70656505, compoundYield 48.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

1-Ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine-7-carbaldehyde (0.423 g) and acetic acid (0.14 g) were added to a 1,2-dichloroethane solution (10 ml) of N-(4-methylthiazol-5-ylmethyl)-N-(2-pyridin-3-ylethyl)amine (0.36 g). The mixture was stirred at room temperature for 30 minutes. Sodium triacetoxyborohydride (0.48 g) was added, and the mixture was stirred at room temperature overnight. The reaction liquid was condensed under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=100:0→50:50). The purified product was condensed under reduced pressure. The residue was washed with diethyl ether, and dried to give the title compound (0.37 g) as a white powder.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. customThe reaction liquid
  3. customcondensed under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=100:0→50:50)
  5. customcondensed under reduced pressure
  6. washThe residue was washed with diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-32f023bb63584d328554f692b0b18111
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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