6-Bromo-3-methyl[1,2,4]triazolo[4,3-a]pyridine → HCID 91826310, compound

HRID 873829Notes

Reaction equation

HRID 873829 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:15]3[C:11](=[N:12][N:13]([CH3:17])[C:14]=3[CH3:16])[C:10](=[O:18])[NH:9]2)=[CH:4][CH:3]=1.Br[C:20]1[CH:21]=[CH:22][C:23]2[N:24]([C:26]([CH3:29])=[N:27][N:28]=2)[CH:25]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[C:15]3[C:11](=[N:12][N:13]([CH3:17])[C:14]=3[CH3:16])[C:10](=[O:18])[N:9]2[C:20]2[CH:21]=[CH:22][C:23]3[N:24]([C:26]([CH3:29])=[N:27][N:28]=3)[CH:25]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 177500996-Bromo-3-methyl[1,2,4]triazolo[4,3-a]pyridineHCID 117702807HCID 117702807, compound

Product 1

HCID 91826310HCID 91826310, compound

Procedure

The title compound was prepared in analogy to the procedure described in Example 24 using 4-(4-chlorophenyl)-2,3-dimethyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(2H)-one (Step 25.6) and 6-bromo-3-methyl[1,2,4]triazolo-[4,3-a]pyridine. After purification by silica gel column chromatography, the resulting residue was purified by SFC (Thar 100; column: PFP, 25 cm, Ø 3 cm, 5 μm, 60 Å; gradient: 10% B for 1 min, 10-15% B in 6 min, 15-50% B in 1 min, 50% B for 1.5 min, 50%-10% B in 1 min, 10% B for 0.5 min; A: scCO2, B: MeOH; flow: 100 mL/min). The residue was triturated in Et2O. tR: 3.26 min (HPLC 1); tR: 0.77 min (LC-MS 2); ESI-MS: 393 [M+H]+ (LC-MS 2); Rf=0.37 (CH2Cl2/MeOH 9:1); 1H NMR (400 MHz, DMSO-d6) δ ppm 2.11 (s, 3H) 2.64 (s, 3H) 3.88 (s, 3H) 6.49 (s, 1H) 7.35 (s, 4H) 7.47-7.52 (m, 1H) 7.65-7.70 (m, 1H) 8.64 (s, 1H).

Workup

  1. customAfter purification by silica gel column chromatography
  2. customthe resulting residue was purified by SFC (Thar 100
  3. wait10-15% B in 6 min
  4. wait15-50% B in 1 min
  5. wait50% B for 1.5 min
  6. wait50%-10% B in 1 min
  7. wait10% B for 0.5 min
  8. customThe residue was triturated in Et2O

Sources & evidence

ORD record
ord-ce8215e3da63457b852c3f4a81b0cb68
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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