2,3-Diaminopyridine → HCID 69280097, compound

HRID 968493Notes

Reaction equation

HRID 968493 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:14][CH2:13][CH2:12][CH:11]([C:15]#[N:16])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N[C:18]1[C:23]([NH2:24])=[CH:22][CH:21]=[CH:20][N:19]=1>>[C:1]1([CH2:7][N:8]2[CH2:14][CH2:13][CH2:12][CH:11]([C:15]3[NH:24][C:23]4[C:18]([N:16]=3)=[N:19][CH:20]=[CH:21][CH:22]=4)[CH2:10][CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 99562,3-DiaminopyridineHCID 69280233HCID 69280233, compound

Product 1

HCID 69280097HCID 69280097, compoundYield 22.1%

Conditions

Temperature
180 °C

Procedure

Polyphosphoric acid (PPA) (10 g) was heated to 160° C. Intermediate (1) (0.0467 mol) and 2,3-diaminopyridine (0.0513 mol) were added. The mixture was stirred at 180° C. for 1 hour, poured out on K2CO3 solid and ice, washed with K2CO3 10% and extracted with DCM. The aqueous layer was washed with DCM. The organic layer was dried, filtered and the solvent was evaporated.This fraction was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 94/6/0.5). The pure fractions were collected and the solvent was evaporated. Part of this fraction (6 g) was crystallized from DIPE and 2-propanone. The precipitate was filtered off and dried, yielding 3.16 g of (±)-2-[hexahydro-1-(phenylmethyl)-1H-azepin-4-yl]-1H-imidazo[4,5-b]pyridine (compound 69).

Workup

  1. additionpoured out on K2CO3 solid and ice
  2. washwashed with K2CO3 10%
  3. extractionextracted with DCM
  4. washThe aqueous layer was washed with DCM
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. customwas purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 94/6/0.5)
  8. customThe pure fractions were collected
  9. customthe solvent was evaporated
  10. customPart of this fraction (6 g) was crystallized from DIPE and 2-propanone
  11. filtrationThe precipitate was filtered off
  12. customdried

Sources & evidence

ORD record
ord-ef906a35d91842b6adae0ebc31bf16c8
Source dataset
uspto-grants-2007_12
Patent number
US07304052B2

Reaction notes

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