Trifluoroacetic acid → HCID 67313244, compound

HRID 1890334Notes

Reaction equation

HRID 1890334 reaction equation
[CH2:1]([O:8][C:9]1[N:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=2)[C:12]([NH2:23])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:24]#[C:25]Br.C(O)(C(F)(F)F)=O.C([O-])([O-])=O.[Na+].[Na+]>O>[CH2:1]([O:8][C:9]1[N:14]=[C:13]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=3)[C:25]([NH2:24])=[N:23][C:12]2=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 10476Cyanogen BromideHCID 67313581HCID 67313581, compound

Product 1

HCID 67313244HCID 67313244, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 6-(benzyloxy)-N2-(4-bromophenyl)pyridine-2,3-diamine (3.86 g, 10.4 mmol) in H2O was added cyanogen bromide (1.44 g, 13.5 mmol) and TFA (200 μL). The reaction mixture was stirred at room temperature for 2.5 h, added 2 M aqueous Na2CO3 and extracted with DCM. The organic extract was dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography to give 5-(benzyloxy)-3-(4-bromophenyl)-3H-imidazo[4,5-b]pyridin-2-amine intermediate. The benzyl group was removed in a similar manner as the one described in Example 1.102 to give the title compound. LCMS m/z=305.1 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 6.22 (broad s, 2H), 6.29 (d, J=8.2 Hz, 1H), 7.39-7.46 (m, 3H), 7.77 (m, 2H), 9.96 (s, 1H).

Workup

  1. extractionextracted with DCM
  2. extractionThe organic extract
  3. dry with materialwas dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-c4747c67791e4370bbcc1165d280ae1e
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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