Sodium Acetate → HCID 68712147, compound

HRID 1159810Notes

Reaction equation

HRID 1159810 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].FC(F)(F)C(O)=O.[CH3:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:35][N:36]2[CH2:41]CN[CH2:38][CH2:37]2)=[C:21]2[C:25]=1[N:24]([S:26]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)(=[O:28])=[O:27])[CH:23]=[CH:22]2.Cl.N1CCC1.C([O-])(=O)C.[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[N:36]1([CH2:35][C:20]2[CH:19]=[CH:18][C:17]([O:16][CH3:15])=[C:25]3[C:21]=2[CH:22]=[CH:23][N:24]3[S:26]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)(=[O:28])=[O:27])[CH2:41][CH2:38][CH2:37]1

Participants

6

Reactant 4

HCID 517045Sodium AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 12308726Azetidine hydrochlorideHCID 86618252HCID 86618252, compound

Product 1

HCID 68712147HCID 68712147, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

1-Benzenesulfonyl-7-methoxy-1H-indole-4-carbaldehyde (20 mg, 0.06 mmol prepared as in Example 79) azetidine hydrochloride (30 mg, 0.32 mmol) and sodium acetate (26 mg, 0.32 mmol) were mixed in 1,2-dichloroethane (1 mL), and stirred at 40° for 1 h, cooled to room temp followed by addition of sodium triacetoxyborohydride (22 mg, 0.1 mmol). The mixture was stirred over night. No remaining starting material according to LCMS. The mixture was evaporated, dissolved in DMF, filtered an purified on prep HPLC YMC 40 mL/min 22-50 mL MeCN over 16 min. Obtained 9.8 mg (43%). MS ESI+ for C19H20N2O3S m/z 357 (M+H)+.

Workup

  1. stirringThe mixture was stirred over night
  2. customThe mixture was evaporated
  3. dissolutiondissolved in DMF
  4. filtrationfiltered
  5. customan purified on prep HPLC YMC 40 mL/min 22-50 mL MeCN over 16 min
  6. customObtained 9.8 mg (43%)

Sources & evidence

ORD record
ord-9ad7159d18884d3f90114c5667584e71
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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