Hydrochloric Acid → HCID 57968770, compound

HRID 1664380Notes

Reaction equation

HRID 1664380 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-edd70faa3b9d41bdadabcf0d929236bc
Source dataset
uspto-grants-2011_10
Patent number
US08039450B2

Reaction notes

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