4,6-Dimethoxypyridin-3-amine → HCID 71227723, compound

HRID 715532Notes

Reaction equation

HRID 715532 reaction equation
[CH3:1][C@:2]1([CH2:10][N:11]2[C:15]3[CH:16]=[C:17]([C:20]#[N:21])[CH:18]=[CH:19][C:14]=3[N:13]=[CH:12]2)[CH2:9][CH2:8][CH2:7][C@:4]2([O:6][CH2:5]2)[CH2:3]1.[CH3:22][O:23][C:24]1[CH:29]=[C:28]([O:30][CH3:31])[N:27]=[CH:26][C:25]=1[NH2:32]>C(O)(C)C>[CH3:22][O:23][C:24]1[CH:29]=[C:28]([O:30][CH3:31])[N:27]=[CH:26][C:25]=1[NH:32][CH2:5][C@:4]1([OH:6])[CH2:7][CH2:8][CH2:9][C@@:2]([CH2:10][N:11]2[C:15]3[CH:16]=[C:17]([C:20]#[N:21])[CH:18]=[CH:19][C:14]=3[N:13]=[CH:12]2)([CH3:1])[CH2:3]1

Participants

4

Reactant 2

HCID 534078224,6-Dimethoxypyridin-3-amineHCID 86716577((3S,5S)-5-methyl-1-oxaspiro[2.5]octan-5-ylmethyl)-1H-benzo[d]imidazole-6-carbonitrile

Product 1

HCID 71227723HCID 71227723, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 1-(((3S,5S)-5-methyl-1-oxaspiro[2.5]octan-5-yl)methyl)-1H-benzo[d]imidazole-6-carbonitrile (100 mg, 0.355 mmol) and 4,6-bis(methyloxy)-3-pyridinamine (110 mg, 0.711 mmol) in isopropanol (10 mL) was heated to reflux overnight. The reaction mixture was cooled to RT, and solvent was removed. The residue was redissolved in DCM and hexane was added. The solvent was removed, and the residue was purified via silica gel chromatography (ISCO, 40 g Silica, 40 mL/min, 0%-10% MeOH/CH2Cl2). Fractions with product were collected and concentrated to afford 1-(((1S,3S)-3-(((4,6-dimethoxypyridin-3-yl)amino)methyl)-3-hydroxy-1-methylcyclohexaneyl)methyl)-1H-benzo[d]imidazole-6-carbonitrile (100 mg, 64.6% yield). MS (m/z) 436 (M+H+).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customsolvent was removed
  4. dissolutionThe residue was redissolved in DCM
  5. additionhexane was added
  6. customThe solvent was removed
  7. customthe residue was purified via silica gel chromatography (ISCO, 40 g Silica, 40 mL/min, 0%-10% MeOH/CH2Cl2)
  8. customFractions with product were collected
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-569fe55be3df4a03850c23e2254ccd48
Source dataset
uspto-grants-2015_11
Patent number
US09187464B2

Reaction notes

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