Sodium triacetoxyborohydride → HCID 86684772, compound

HRID 579199Notes

Reaction equation

HRID 579199 reaction equation
[CH:1]1([C@@H:7]2[CH2:12][NH:11][CH2:10][C:9](=[O:13])[N:8]2[C:14]2[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[S:16][C:15]=2[C:25]([OH:27])=[O:26])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F:28][C:29]1[C:30]([N:37]2[CH2:42][CH2:41][O:40][CH2:39][CH2:38]2)=[C:31]([CH:34]=[CH:35][CH:36]=1)[CH:32]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C.CO>[CH:1]1([C@@H:7]2[CH2:12][N:11]([CH2:32][C:31]3[CH:34]=[CH:35][CH:36]=[C:29]([F:28])[C:30]=3[N:37]3[CH2:38][CH2:39][O:40][CH2:41][CH2:42]3)[CH2:10][C:9](=[O:13])[N:8]2[C:14]2[CH:18]=[C:17]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[S:16][C:15]=2[C:25]([OH:27])=[O:26])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 261887513-Fluoro-2-(morpholin-4-yl)benzaldehydeHCID 66684918HCID 66684918, compound

Product 1

HCID 86684772HCID 86684772, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

A solution of 3-((R)-2-cyclohexyl-6-oxo-piperazin-1-yl)-5-phenyl-thiophene-2-carboxylic acid (50.0 mg, 0.13 mmol, 1.0 equiv) and 3-fluoro-2-morpholinobenzaldehyde (108.8 mg, 0.52 mmol, 4.0 equiv) in acetic acid (0.2 mL) and methanol (0.5 mL) was stirred at room temperature for 60 minutes. Then sodium triacetoxyborohydride (110.2 mg, 0.52 mmol, 4.0 equiv) was added to the mixture and the resulting mixture was stirred at 75° C. for 3 hours. The solvent was removed by Genevac and the residue was dissolved in EtOAc (6 mL). The organic phase was washed by brine (3 mL), dried over Na2SO4 and concentrated. The residue was purified by HPLC (0.1% NH4OH) to afford the product (9 mg, 12%). MS: 577.2 [M−H+].

Workup

  1. customThe solvent was removed by Genevac
  2. dissolutionthe residue was dissolved in EtOAc (6 mL)
  3. washThe organic phase was washed by brine (3 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by HPLC (0.1% NH4OH)

Sources & evidence

ORD record
ord-48ae17ee13b5499cb2437c6f9cf4d8f0
Source dataset
uspto-grants-2015_05
Patent number
US09040690B2

Reaction notes

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