Trifluoroacetic acid → HCID 178420750, compound

HRID 1798911Notes

Reaction equation

HRID 1798911 reaction equation
COC1C=CC(C[N:8]2[CH2:17][C:16]3[CH2:15][CH2:14][C:13]4=[N:18][NH:19][N:20]=[C:11]([C:12]=34)[C:10]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[N:9]2)=CC=1.FC(F)(F)C(O)=O>>[N:18]1[NH:19][N:20]=[C:11]2[C:10]([N:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)=[N:9][NH:8][CH2:17][C:16]3[CH2:15][CH2:14][C:13]=1[C:12]2=3

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178490751HCID 178490751, compound

Product 1

HCID 178420750HCID 178420750, compound

Conditions

Temperature
65 °C

Procedure

To 4-(6-(4-methoxybenzyl)-6,7,8,9-tetrahydro-2H-1,2,3,5,6-pentaazabenzo[cd]azulen-4-yl)morpholine 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 residue was dissolved in DMSO. This was then purified using reverse phase column chromatography using a Maccel AQ C18 column and a gradient of 1-95% ACN/water containing 0.05% trifluoroacetic acied, to yield 4-(6,7,8,9-tetrahydro-2H-1,2,3,5,6-pentaazabenzo[cd]azulen-4-yl)morpholine, compound 243. LC/MS. LC-Mass: 261 (M+1)

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionthe crude residue was dissolved in DMSO
  3. customThis was then purified

Sources & evidence

ORD record
ord-cd9b18ea40ca4199b0a7d27a2733c92c
Source dataset
uspto-grants-2013_01
Patent number
US08343983B2

Reaction notes

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