Hydrochloric Acid → HCID 67439719, compound

HRID 1483683Notes

Reaction equation

HRID 1483683 reaction equation
C([C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][C:27]=1[B:28]1[O:32]C(C)(C)[C:30](C)(C)[O:29]1)[O:6][C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[C:9]([O:15][CH2:16][CH2:17][O:18]C2CCCCO2)[N:8]=1)=O.[BH4-].[Na+].Cl>CO>[OH:32][B:28]1[C:27]2[CH:26]=[CH:25][C:5]([O:6][C:7]3[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[C:9]([O:15][CH2:16][CH2:17][OH:18])[N:8]=3)=[CH:4][C:3]=2[CH2:30][O:29]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 86636433HCID 86636433, compound

Product 1

HCID 67439719HCID 67439719, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-[3-formyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxy]-2-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-nicotinonitrile (2.5 g, 5.15 mmol) in methanol (15 mL) at 0° C. was added sodium borohydride (0.38 g, 10.32 mmol). After 1 h at rt, the solution was cooled in an ice bath and 2M HCl was added until pH reached to 3-4. The resulting mixture was stirred at 0° C. for 2 h and then at room temperature for 30 min. The solvent was removed under reduced pressure purification was accomplished by reverse phase prep HPLC using CH3CN/H2O (0.1% AcOH) as the eluent to yield the title compound D99 (1.0 g, 40%) as white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.23 (s, 1H), 8.22 (d, J=8.2 Hz, 1H), 7.77 (d, J=8.2 Hz, 1H), 7.27 (s, 1H), 7.18 (d, J=8.2 Hz, 1H), 6.66 (d, J=8.6 Hz, 1H), 4.97 (s, 2H), 4.82 (t, 1H), 4.12 (t, J=4.9 Hz, 2H), 3.73-3.50 (m, 2H); MS (ES) m/z: 313 (M+1)+; HPLC purity 98.78% (Maxplot), 98.58% (220 nm).

Workup

  1. temperaturethe solution was cooled in an ice bath
  2. waitat room temperature for 30 min
  3. customThe solvent was removed under reduced pressure purification

Sources & evidence

ORD record
ord-f296c4498fe24d5a9eefc2ffc62ccf3b
Source dataset
uspto-grants-2016_08
Patent number
US09416146B2

Reaction notes

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