Hydrochloric Acid → HCID 57968770, compound

HRID 1483690Notes

Reaction equation

HRID 1483690 reaction equation
C([C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][C:22]=1[B:23]1[O:27]C(C)(C)[C:25](C)(C)[O:24]1)[O:6][C:7]1[N:14]=[C:13]([NH:15][CH2:16][CH2:17][O:18][CH3:19])[CH:12]=[CH:11][C:8]=1[C:9]#[N:10])=O.[BH4-].[Na+].Cl>CO>[OH:27][B:23]1[C:22]2[CH:21]=[CH:20][C:5]([O:6][C:7]3[N:14]=[C:13]([NH:15][CH2:16][CH2:17][O:18][CH3:19])[CH:12]=[CH:11][C:8]=3[C:9]#[N:10])=[CH:4][C:3]=2[CH2:25][O:24]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 57968898HCID 57968898, compound

Product 1

HCID 57968770HCID 57968770, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a clear solution of 2-[3-formyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxy]-6-(2-methoxy-ethylamino)-nicotinonitrile (10) (440 mg, 1.04 mmol) in MeOH (anhydrous, 100 mL) was slowly added NaBH4 (120 mg, 3.12 mmol). The reaction was stirred at room temperature for 4 hours, before the addition of HCl solution (1 M, 50 mL). The stirring was kept at room temperature overnight. Then the solution was slowly concentrated in vacuo. Purification was accomplished by preparative HPLC to afford the title compound (108 mg, 32% yield) as a white lyophilizate. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.23 (br. s., 1H), 7.86 (br. s., 1H), 7.79-7.68 (m, 2H), 7.24 (s, 1H), 7.18-7.13 (m, 1H), 6.30 (d, J=8.6 Hz, 1H), 4.98 (s, 2H), 3.20 (d, J=1.6 Hz, 2H), 3.17-3.06 (m, 5H); ES-MS m/z=326 (M+H)+; HPLC: 99.39% (220 nm), 99.24% (MaxPlot).

Workup

  1. concentrationThen the solution was slowly concentrated in vacuo
  2. customPurification

Sources & evidence

ORD record
ord-b839993333544fe58fe5ab7b3d5ef278
Source dataset
uspto-grants-2016_08
Patent number
US09416146B2

Reaction notes

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