2-Methoxyethylamine → HCID 58032616, compound

HRID 1046901Notes

Reaction equation

HRID 1046901 reaction equation
Br[CH2:2][C:3]1[N:4]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=2)[C:5]2[N:6]([N:22]=[N:23][N:24]=2)[CH:7]([C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=2)[C:8]=1[C:9](OCC)=[O:10].[CH3:35][O:36][CH2:37][CH2:38][NH2:39]>CC(C)=O>[CH3:35][O:36][CH2:37][CH2:38][N:39]1[C:9](=[O:10])[C:8]2[CH:7]([C:14]3[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=3)[N:6]3[N:22]=[N:23][N:24]=[C:5]3[N:4]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:33])([F:34])[F:32])[CH:26]=3)[C:3]=2[CH2:2]1

Participants

4

Reactant 2

HCID 80182-Methoxyethylamine2×HCID 58032604HCID 58032604, compound

Product 1

HCID 58032616HCID 58032616, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ethyl 5-(bromomethyl)-7-(4-cyanophenyl)-4-[3-(trifluoromethyl)phenyl]-4,7-dihydrotetrazolo-[1,5-a]pyrimidine-6-carboxylate (35.3 mg, 66.1 μmol) was initially charged in acetone (1.0 ml). 2-Methoxyethylamine (12.4 mg, 4 μl, 165 μmol, 2.5 eq.) was added dropwise, and the mixture was then stirred at RT overnight. After addition of more 2-methoxyethylamine (9.9 mg, 132 μmol, 2 eq.), the mixture was stirred at RT for a further 5 h. The reaction mixture was then concentrated under reduced pressure and the residue was purified by preparative HPLC (Kromasil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA). After lyophilization, the product was obtained as a solid (13 mg, 41% of theory).

Workup

  1. stirringthe mixture was stirred at RT for a further 5 h
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. customthe residue was purified by preparative HPLC (Kromasil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA)
  4. customAfter lyophilization, the product was obtained as a solid (13 mg, 41% of theory)

Sources & evidence

ORD record
ord-8574ad473d39427ea2a214965a1cae7b
Source dataset
uspto-grants-2013_10
Patent number
US08569314B2

Reaction notes

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