Potassium Carbonate → HCID 118364806, compound

HRID 1478578Notes

Reaction equation

HRID 1478578 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[C:11]3[N:13]([CH2:16][C@@H:17]4[CH2:22][N:21]([C:23]5[N:28]=[CH:27][C:26]([CH:29]=O)=[CH:25][N:24]=5)[CH2:20][CH2:19][O:18]4)[N:14]=[N:15][C:10]3=[N:9][CH:8]=2)[CH:4]=[N:3]1.[CH3:31][N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.CC(O)=O>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[C:11]3[N:13]([CH2:16][C@H:17]4[O:18][CH2:19][CH2:20][N:21]([C:23]5[N:24]=[CH:25][C:26]([CH2:29][N:35]6[CH2:36][CH2:37][N:32]([CH3:31])[CH2:33][CH2:34]6)=[CH:27][N:28]=5)[CH2:22]4)[N:14]=[N:15][C:10]3=[N:9][CH:8]=2)[CH:4]=[N:3]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 118364814HCID 118364814, compound

Product 1

HCID 118364806HCID 118364806, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

(S)-2-(2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)morpholino)pyrimidine-5-carboaldehyde 16 mg(0.033 mmol) was dissolved in CH2Cl2 2 ml, and 1-methylpiperazine 7.4 μl (0.066 mmol), AcOH 2.3 μl, and NaBH(OAc)3 11 mg (0.05 mmol) were added, followed by stirring at room temperature overnight. After the completion of the reaction, the reaction mixture was adjusted to pH 8 with aq. K2CO3 (5%), and extracted with H2O, EA, and brine, followed by drying (Na2SO4), filtration, and concentration under reduced pressure. The residue was purified by column chromatography (MeOH:MC=1:10), to give (S)-2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)-4-(5-((4-methylpiperazin-1-yl)methyl)pyrimidin-2-yl)morpholine 14.1 mg, (76%).

Workup

  1. customAfter the completion of the reaction
  2. extractionextracted with H2O, EA, and brine
  3. customby drying
  4. filtration(Na2SO4), filtration, and concentration under reduced pressure
  5. customThe residue was purified by column chromatography (MeOH:MC=1:10)

Sources & evidence

ORD record
ord-853b5d372a93432da867834ffee5f4e2
Source dataset
uspto-grants-2016_08
Patent number
US09403831B2

Reaction notes

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