Diisopropylethylamine → HCID 178488088, compound

HRID 1428398Notes

Reaction equation

HRID 1428398 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:13])[CH2:9][C:10](O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.Cl.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([NH2:25])[C:21]([NH2:24])=[CH:22][CH:23]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CCOC(C)=O.CN(C=O)C>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]2[NH:24][C:10]([CH2:9][N:8]([CH3:13])[C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[N:25][C:20]=2[CH:19]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-HCID 30851614-Methoxybenzene-1,2-diamine dihydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 178488088HCID 178488088, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of N-(tert-butoxycarbonyl)-N-methylglycine (1.00 g), 4-methoxybenzene-1,2-diamine dihydrochloride (1.16 g) and DMF (25 mL) were added HATU (2.41 g) and DIPEA (4.5 mL), followed by stirring at room temperature overnight. The reaction mixture was diluted with EtOAc, and washed with water and brine in this order. The organic layer was dried over Na2SO4 and then concentrated under reduced pressure. To the residue was added acetic acid (20 mL), followed by heating and stirring at 80° C. for 3 hours, and then concentrating under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: Hex/EtOAc=80/20-20/80) to obtain tert-butyl [(5-methoxy-1H-benzimidazol-2-yl)methyl]methylcarbamate (1.22 g).

Workup

  1. washwashed with water and brine in this order
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. additionTo the residue was added acetic acid (20 mL)
  5. temperatureby heating
  6. stirringstirring at 80° C. for 3 hours
  7. concentrationconcentrating under reduced pressure
  8. customThe residue was purified by basic silica gel column chromatography (eluent: Hex/EtOAc=80/20-20/80)

Sources & evidence

ORD record
ord-c623af38d9474133bcbf89c1819ad1a7
Source dataset
uspto-grants-2015_01
Patent number
US08937087B2

Reaction notes

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