2-Pentanol → HCID 71240769, compound

HRID 1842804Notes

Reaction equation

HRID 1842804 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)[CH:5]=[CH:4][N:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:29][O:30][C:31]1[CH:37]=[C:36]([C:38]2[CH2:39][CH2:40][N:41]([CH3:44])[CH2:42][CH:43]=2)[C:35]([N+:45]([O-:47])=[O:46])=[CH:34][C:32]=1[NH2:33].CC(O)CCC>CN(C=O)C>[CH3:29][O:30][C:31]1[CH:37]=[C:36]([C:38]2[CH2:43][CH2:42][N:41]([CH3:44])[CH2:40][CH:39]=2)[C:35]([N+:45]([O-:47])=[O:46])=[CH:34][C:32]=1[NH:33][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 223862-PentanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 717430803-(2-Chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridine2×HCID 866773252-methoxy-4-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-5-nitroaniline2×

Product 1

HCID 71240769HCID 71240769, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(2-chloropyrimidin-4-yl)pyrazolo[1,5-a]pyridine (Intermediate 152, 256 mg, 1.00 mmol), p-toluene sulphonic acid monohydrate (271 mg, 1.43 mmol) and 2-methoxy-4-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-5-nitroaniline (Intermediate 3, 250 mg, 0.95 mmol) and 2-pentanol (12 mL) was heated at reflux for 4 h under an atmosphere of N2. The mixture was then concentrated in vacuo and the residue was dissolved in CH3OH. This solution was purified by ion exchange chromatography, using an SCX column, eluting with 7M methanolic ammonia. Fractions containing the desired product were concentrated in vacuo to give a residue that was dissolved into hot DMF (10 mL). This solution was filtered and concentrated in vacuo to provide a gum that was triturated with CH3CN (10 mL) to give the title compound (285 mg, 66%) as a yellow powder; 1H NMR: 2.36 (5H, s), 2.67 (2H, s), 3.07 (2H, s), 4.02 (3H, s), 5.66 (1H, s), 7.00 (1H, s), 7.12 (1H, t), 7.41 (1H, m), 7.45 (1H, m), 8.45 (2H, t), 8.59 (1H, d), 8.83 (2H, t), 8.90 (1H, s); m/z: ES− M-H− 456.

Workup

  1. temperatureat reflux for 4 h under an atmosphere of N2
  2. concentrationThe mixture was then concentrated in vacuo
  3. dissolutionthe residue was dissolved in CH3OH
  4. customThis solution was purified by ion exchange chromatography
  5. washeluting with 7M methanolic ammonia
  6. additionFractions containing the desired product
  7. concentrationwere concentrated in vacuo
  8. customto give a residue that
  9. filtrationThis solution was filtered
  10. concentrationconcentrated in vacuo
  11. customto provide a gum that
  12. customwas triturated with CH3CN (10 mL)

Sources & evidence

ORD record
ord-794300b82d464c71973db3d9167ecc01
Source dataset
uspto-grants-2015_02
Patent number
US08946235B2

Reaction notes

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