Diisopropylethylamine → HCID 44561082, compound

HRID 490898

Reaction equation

HRID 490898 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[N:13]([CH2:16][CH3:17])[N:14]=[CH:15][C:3]=12.[CH3:18][NH:19][CH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.C(N(C(C)C)CC)(C)C>CC#N>[CH2:16]([N:13]1[C:4]2=[N:5][CH:6]=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:2]([N:19]([CH3:18])[CH:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[C:3]2[CH:15]=[N:14]1)[CH3:17]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 69919504-(Methylamino)tetrahydro-2H-pyranHCID 10491120ethyl 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

Product 1

HCID 44561082HCID 44561082, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Intermediate 1 (1.2 g, 4.76 mmol), Intermediate 50 (0.79 g, 5.2 mmol) and diisopropylethylamine (4 ml, 24 mmol) in MeCN (8 ml) was heated at 70° C. for 24 hours. The solvent was removed in vacuo and the residue partitioned between DCM and water. The organic phase was concentrated in vacuo and the residue chromatographed on silica (50 g) eluting with cyclohexane:ethyl acetate (2:1 followed by 1:1 then 1:2). Appropriate fractions were combined and evaporated to give Intermediate 51 as a brown oil (1.21 g). LCMS showed MH+=334; TRET=2.61 min.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between DCM and water
  3. concentrationThe organic phase was concentrated in vacuo
  4. customthe residue chromatographed on silica (50 g)
  5. washeluting with cyclohexane:ethyl acetate (2:1
  6. customevaporated

Sources & evidence

ORD record
ord-6bb30160f5c549bca1f5b8d0dc14c418
Source dataset
uspto-grants-2009_05
Patent number
US07528148B2

Linked notes

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