Sodium Bicarbonate → HCID 58504299, compound

HRID 2407793Notes

Reaction equation

HRID 2407793 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[S:7][C:8]([CH:11]=O)=[CH:9][N:10]=1.[NH2:13][C:14]1[C:19]([C:20]#[N:21])=[C:18]([O:22][CH2:23][CH3:24])[N:17]=[C:16]([C:25]([NH:27][CH2:28][CH:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[O:26])[CH:15]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClC(Cl)C.C(O)(=O)C>[NH2:13][C:14]1[C:19]([C:20]#[N:21])=[C:18]([O:22][CH2:23][CH3:24])[N:17]=[C:16]([C:25]([NH:27][CH2:28][CH:29]2[CH2:34][CH2:33][N:32]([CH2:11][C:8]3[S:7][C:6]([C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)=[N:10][CH:9]=3)[CH2:31][CH2:30]2)=[O:26])[CH:15]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 2356065554986-99-1HCID 58503970HCID 58503970, compound

Product 1

HCID 58504299HCID 58504299, compoundYield 31.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 63651,1-DichloroethaneSolvent

Procedure

The compound prepared in Example 333 (31 mg) and the compound prepared in Example 334 (48 mg) were combined in dichloroethane (1.6 mL) and acetic acid (0.054 mL) was added. Sodium triacetoxyborohydride (0.101 g) was then added. The reaction mixture was stirred at ambient temperature for 17 hours. It was then treated with saturated sodium bicarbonate and extracted with dichloromethane. The combined organics were dried over magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:methanol=98:2) to obtain the title compound (24 mg) having the following physical data.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined organics were dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography on silica gel (ethyl acetate:methanol=98:2)

Sources & evidence

ORD record
ord-5251561e49cb4e2e9605629eced14858
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

Loading…