Propanal → HCID 67456847, compound

HRID 1853021Notes

Reaction equation

HRID 1853021 reaction equation
Cl.[CH3:2][N:3]1[CH:7]=[C:6]([C:8]2[N:13]=[C:12]([C:14]3[CH:15]=[N:16][N:17]([C:19]4([CH2:23][C:24]#[N:25])[CH2:22][NH:21][CH2:20]4)[CH:18]=3)[N:11]3[CH:26]=[CH:27][N:28]=[C:10]3[CH:9]=2)[CH:5]=[N:4]1.C(#N)C.C(N(CC)CC)C.[CH:39](=O)[CH2:40][CH3:41].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[CH3:2][N:3]1[CH:7]=[C:6]([C:8]2[N:13]=[C:12]([C:14]3[CH:15]=[N:16][N:17]([C:19]4([CH2:23][C:24]#[N:25])[CH2:22][N:21]([CH2:39][CH2:40][CH3:41])[CH2:20]4)[CH:18]=3)[N:11]3[CH:26]=[CH:27][N:28]=[C:10]3[CH:9]=2)[CH:5]=[N:4]1

Participants

6

Reactant 5

HCID 527PropanalHCID 6342AcetonitrileHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 674570102-(3-(4-(7-(1-Methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile hydrochloride

Product 1

HCID 67456847HCID 67456847, compoundYield 51%

Procedure

In a 2 mL flask, 2-(3-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile hydrochloride (Example 62; 15 mg, 0.035 mmol) was suspended in acetonitrile (350 μL, 0.035 mmol). To this was added triethylamine (19 μL, 0.14 mmol), followed by propionaldehyde (25 μL, 0.35 mmol). After stirring for 30 minutes, NaBH(OAc)3 (37 mg, 0.17 mmol) was added. After the reaction was complete, it was quenched with saturated bicarbonate solution and extracted with EtOAc. The organic layer was washed with brine, dried with MgSO4, filtered and concentrated in vacuo. The residue was purified by reverse phase HPLC using a 0-100% acetonitrile/water gradient to afford 2-(3-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo-[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)-1-propylazetidin-3-yl)acetonitrile (7.1 mg, 51% yield) as a white solid. MS (apci) m/z=402.2 (M+H).

Workup

  1. customit was quenched with saturated bicarbonate solution
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-db1acc5dd08c439681bcc161ec0ef8f5
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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