Sodium borohydride → HCID 178479780, compound

HRID 2219233Notes

Reaction equation

HRID 2219233 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:15][CH2:16][CH:17]=O)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:14])[CH:7]=1.[Cl-].[Na+].[NH2:21][CH2:22][CH2:23][NH:24][S:25]([C:28]1[C:29]2[CH:30]=[CH:31][N:32]=[C:33]([OH:38])[C:34]=2[CH:35]=[CH:36][CH:37]=1)(=[O:27])=[O:26].[BH4-].[Na+]>CO>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:15][CH2:16][CH2:17][NH:21][CH2:22][CH2:23][NH:24][S:25]([C:28]2[C:29]3[CH:30]=[CH:31][N:32]=[C:33]([OH:38])[C:34]=3[CH:35]=[CH:36][CH:37]=2)(=[O:26])=[O:27])=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:14])[CH:7]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 86610936HCID 86610936, compoundHCID 178511378HCID 178511378, compound

Product 1

HCID 178479780HCID 178479780, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A 6.0 mL of the (5,2′-dichloro-biphenyl-2-yloxy)-acetaldehyde stock solution (1.88 mmol) is added to a stirred mixture of 1-hydroxy-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide sodium chloride (438 mg, 1.34 mmol) and 4 Å molecular sieve (400 mg) in anhydrous CH3OH (8 mL) at ambient temperature under nitrogen. The resultant mixture is stirred for 16 hours. After being cooled to 0° C., the mixture is treated with powdered sodium borohydride (112 mg, 2.95 mmol), then stirred at 0° C. for 1 hour and at ambient temperature for another 1 hour. After filtration and subsequent concentration in vacuo, the crude product is chromatographed on silica (gradient 5-15% CH3OH in EtOAc) to give the desired product as a gum. It is dissolved in EtOAc (15 mL), filtered and concentrated to give 493 mg (0.926 mmol, 69% yield) of the free amine as a white solid. The free amine is dissolved in EtOAc (3,0 mL) and subsequently treated dropwise with 1N HCl/Et2O (8 mL) to give a white suspension. After filtration and vacuum drying at 50° C., 470 mg (0.8.26 mmol, 89% yield) of the title compound is obtained as a white powder. ESIMS: m/z 532 [(M+H)+, 35Cl, 35Cl], 534 [(M+H)+, 35Cl, 37Cl], 536 [(M+H)+, 37Cl, 37Cl].

Workup

  1. filtrationAfter filtration and subsequent concentration in vacuo
  2. customthe crude product is chromatographed on silica (gradient 5-15% CH3OH in EtOAc)

Sources & evidence

ORD record
ord-467f1a1b42a04f6cb32e0e27b6a0bc38
Source dataset
uspto-grants-2008_08
Patent number
US07414063B2

Reaction notes

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