Sodium cyanoborohydride → HCID 178485596, compound

HRID 1053632Notes

Reaction equation

HRID 1053632 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1)[OH:9].[CH:20]([C:22]1[C:23]([C:27]([NH:29][CH3:30])=[O:28])=[N:24][NH:25][CH:26]=1)=O.[BH3-]C#N.[Na+]>ClCCCl>[OH:9][CH:8]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][CH2:20][C:22]1[C:23]([C:27]([NH:29][CH3:30])=[O:28])=[N:24][NH:25][CH:26]=1

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 64832775HCID 64832775, compoundHCID 178485597HCID 178485597, compound

Product 1

HCID 178485596HCID 178485596, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of product (5-B) (0.4 g 1.6 mmol) in DCE (20 mL) was added product (3-C) (0.25 g, 1.6 mmol) at rt under argon. The reaction was stirred for about 5 h, and then NaBH3CN (0.5 g, 8 mmol) was added and stirred overnight. The reaction was quenched by saturated NH4Cl (20 mL) and extracted with DCM/MeOH (20:1 v/v, 20 mL×2). The combined organic phases were dried over Na2SO4 and concentrated and purified by Prep-HPLC to give compound 4 (22 mg, 5%) as a white solid. 1H NMR (300 MHz, d-DMSO): δ 13.04 (br, 1H), 8.14-7.32 (m, 9H), 7.04-6.36 (m, 4H), 5.98-5.85 (m, 2H), 4.47 (d, 2H), 2.72 (d, 3H). LC-MS (M+H)+=387. 1H-NMR (in DMSO), LC-MS, MS, and HPLC (column: Thermo, 2.4 μm, 4.6×100 mm; mobile phase: H2O (0.05% TFA)-ACN (0.05% TFA), ACN from 10% to 100% in eight minutes; total flow rate: 1.0 mL/min) spectroscopy experiments were conducted to provide the data in FIGS. 3A-3C and FIGS. 4A-4B for compound 4.

Workup

  1. stirringstirred overnight
  2. customThe reaction was quenched by saturated NH4Cl (20 mL)
  3. extractionextracted with DCM/MeOH (20:1 v/v, 20 mL×2)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by Prep-HPLC

Sources & evidence

ORD record
ord-8004f2c95dd94cdf8037f84114c216fe
Source dataset
uspto-grants-2016_07
Patent number
US09394256B2

Reaction notes

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