Trifluoroacetic acid → HCID 178420332, compound

HRID 1798892Notes

Reaction equation

HRID 1798892 reaction equation
[CH2:1]([NH:8][C:9]1[N:10]=[C:11]2[C:20]3[C:15](=[N:16][NH:17][C:18]=3[N:19]=1)[CH2:14][CH2:13][N:12]2CC1C=CC(OC)=CC=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>>[CH2:1]([NH:8][C:9]1[N:10]=[C:11]2[C:20]3[C:15](=[N:16][NH:17][C:18]=3[N:19]=1)[CH2:14][CH2:13][NH:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178490774HCID 178490774, compound

Product 1

HCID 178420332HCID 178420332, compound

Conditions

Temperature
65 °C

Procedure

To N-benzyl-5-(4-methoxybenzyl)-1,3,4,5-tetrahydro-1,2,5,6,8-pentaazaacenaphthylen-7-amine from step-2 was added neat trifluoroacetic acid(1 mL). The reaction mixture was heated at 65° C. for 4-16 h. The reaction mixture was evaporated and the crude reside was dissolved into DMSO. The crude product in DMSO was purified using reverse phase column chromatography using a Maccel AQ C18 column and a gradient of 1-95% ACN/water containing 0.05% trifluoroacetic acid, to yield the desired N-benzyl-1,3,4,5-tetrahydro-1,2,5,6,8-pentaazaacenaphthylen-7-amine in acceptable purities by LC/MS. LC-Mass: m/e 387 (M+1).

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionthe crude reside was dissolved into DMSO
  3. customThe crude product in DMSO was purified

Sources & evidence

ORD record
ord-84a9fe8247e343dd8a37b20f0f5e9b9d
Source dataset
uspto-grants-2013_01
Patent number
US08343983B2

Reaction notes

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