2-Methoxyaniline → HCID 11754871, compound

HRID 2218383Notes

Reaction equation

HRID 2218383 reaction equation
[Cl:1][C:2]1[C:3](Cl)=[C:4]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[CH:13][CH:12]=3)[NH:8][C:5]2=[N:6][CH:7]=1.[CH3:27][O:28][C:29]1[C:30]([NH2:35])=[CH:31][CH:32]=[CH:33][CH:34]=1>C(#N)C.C(O)(=O)C>[Cl:1][C:2]1[C:3]([NH:35][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[O:28][CH3:27])=[C:4]2[NH:10][C:9]([C:11]3[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH2:19][N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[CH:15][CH:16]=3)=[N:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 70002-Methoxyaniline2×HCID 178478272HCID 178478272, compound

Product 1

HCID 11754871HCID 11754871, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
180 °C

Procedure

6,7-Dichloro-2-[4-(2-morpholin-4-ylethoxy)phenyl]-3H-imidazo[4,5-b]pyridine (Example 206) (30 mg) was dissolved in o-anisidine (0.75 ml) and heated in a microwave oven (180° C., 20 min). The resulting mixture was diluted with acetonitrile (1 ml) and acetic acid (0.5 ml) and subjected to semi-preparative HPLC-C18. The fractions containing product (it co-elutes with o-anisidine) were pooled and evaporated in vacuo. The residue was dissolved in EtOAc (20 ml) and washed with 1% aqueous NaHCO3 (10 ml). The organic phase was treated with activated carbon and MgSO4, filtered and evaporated in vacuo. The oily residue was triturated with n-heptane (1 ml) and a few drops of EtOAc, which caused the product to crystallize. It was collected by filtration and washed with EtOAc to give the pure product as a white powder (10 mg, 27%). A second crop (2.9 mg) crystallized from the combined mother liquor and washing liquids.

Workup

  1. customevaporated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc (20 ml)
  3. washwashed with 1% aqueous NaHCO3 (10 ml)
  4. additionThe organic phase was treated with activated carbon and MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe oily residue was triturated with n-heptane (1 ml) and a few drops of EtOAc, which
  8. customto crystallize
  9. filtrationIt was collected by filtration
  10. washwashed with EtOAc

Sources & evidence

ORD record
ord-2e89042ef9fd4e35a5e340c8e94d78c6
Source dataset
uspto-grants-2008_08
Patent number
US07410966B2

Reaction notes

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