Acetic Acid → HCID 46198656, compound

HRID 1930589Notes

Reaction equation

HRID 1930589 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:15]=[C:16]([N:24]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:25][CH2:26][OH:27])[C:17]4[CH2:23][NH:22][CH2:21][CH2:20][C:18]=4[N:19]=3)=[CH:9][CH:8]=2)[CH:4]=[N:3]1.C(O)(=O)C.[CH:38](=O)[CH2:39][CH3:40].C([BH3-])#N.[Na+]>CO>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([NH:13][C:14]3[N:15]=[C:16]([N:24]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:25][CH2:26][OH:27])[C:17]4[CH2:23][N:22]([CH2:38][CH2:39][CH3:40])[CH2:21][CH2:20][C:18]=4[N:19]=3)=[CH:11][CH:12]=2)[CH:4]=[N:3]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 527PropanalHCID 5003444Sodium cyanoborohydrideHCID 59333755HCID 59333755, compound

Product 1

HCID 46198656HCID 46198656, compoundYield 17.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-((2-(4-(1-Methyl-1H-pyrazol-4-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)(phenyl)amino)ethanol (40 mg, 0.09 mmol, Example 38a) was dissolved in methanol (2 mL). Acetic acid (1.037 μL, 0.02 mmol) was added followed by propionaldehyde (0.013 mL, 0.18 mmol). The reaction mixture was stirred for 30 minutes at room temperature before sodium cyanoborohydride (11.39 mg, 0.18 mmol) was added. The solvent was evaporated under reduced pressure, the crude dissolved in few drops of dimethylformamide and acetonitrile, filtered and purified by preparative HPLC yielding 2-((2-(4-(1-methyl-1H-pyrazol-4-yl)phenylamino)-6-propyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)(phenyl)amino)ethanol (7.6 mg, 15.4%) as acetic acid salt.

Workup

  1. additionwas added
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionthe crude dissolved in few drops of dimethylformamide and acetonitrile
  4. filtrationfiltered
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-30c026d6581840d08d62da789817ce37
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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