Hydrochloric Acid → HCID 57968878, compound

HRID 1471545Notes

Reaction equation

HRID 1471545 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][NH:9][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[C:12]([O:18][C:19]2[CH:24]=[CH:23][C:22]([B:25]3[O:29][C:28](C)(C)C(C)(C)[O:26]3)=[C:21](C=O)[CH:20]=2)[N:11]=1)(C)(C)C.C([Si](C)(C)OCCNC1C=CC(C#N)=C(OC2C=CC=C(C=O)C=2)N=1)(C)(C)C.[BH4-].[Na+].Cl>CO>[OH:26][B:25]1[C:22]2[CH:23]=[CH:24][C:19]([O:18][C:12]3[N:11]=[C:10]([NH:9][CH2:8][CH2:7][OH:6])[CH:17]=[CH:16][C:13]=3[C:14]#[N:15])=[CH:20][C:21]=2[CH2:28][O:29]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 57969151HCID 57969151, compoundHCID 86636439HCID 86636439, compound

Product 1

HCID 57968878HCID 57968878, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a clear solution of mixture of 9 and 10 (6-[2-(tert-butyl-dimethyl-silanyloxy)-ethylamino]-2-[3-formyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxy]-nicotinonitrile and 6-[2-(tert-butyl-dimethyl-silanyloxy)-ethylamino]-2-(3-formyl-phenoxy)-nicotinonitrile) in MeOH (anhydrous, 200 mL) was slowly added NaBH4 (0.26 g, 6.9 mmol). The reaction was stirred at room temperature for 4 hours, before the addition of HCl solution (1 M, 30 mL). After overnight at room temperature, the solution was slowly evaporated in vacuo. Purification was accomplished by reverse phase Biotage with 5%-100% MeOH/H2O gradient to afford 120 mg (29% yield) of the title compound as a white solid.

Workup

  1. customthe solution was slowly evaporated in vacuo
  2. customPurification

Sources & evidence

ORD record
ord-c97971c22cad451fb3851ac9e51014d3
Source dataset
uspto-grants-2015_04
Patent number
US09012431B2

Reaction notes

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