Azetidine → HCID 25072858, compound

HRID 656148Notes

Reaction equation

HRID 656148 reaction equation
[CH3:1][C:2]1([CH3:29])[CH2:7][CH:6]([C:8]2[C:16]3[C:11](=[C:12]([C:24]([NH2:26])=[O:25])[CH:13]=[C:14]([C:17]4[CH:21]=[C:20]([CH:22]=O)[S:19][CH:18]=4)[CH:15]=3)[NH:10][CH:9]=2)[CH2:5][CH2:4][S:3]1(=[O:28])=[O:27].[NH:30]1[CH2:33][CH2:32][CH2:31]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CS(C)=O.C(O)(=O)C>[N:30]1([CH2:22][C:20]2[S:19][CH:18]=[C:17]([C:14]3[CH:15]=[C:16]4[C:11](=[C:12]([C:24]([NH2:26])=[O:25])[CH:13]=3)[NH:10][CH:9]=[C:8]4[CH:6]3[CH2:5][CH2:4][S:3](=[O:28])(=[O:27])[C:2]([CH3:1])([CH3:29])[CH2:7]3)[CH:21]=2)[CH2:33][CH2:32][CH2:31]1

Participants

6

Reactant 3

HCID 10422AzetidineHCID 5049666Sodium triacetoxyborohydrideHCID 59332756HCID 59332756, compound

Product 1

HCID 25072858HCID 25072858, compoundYield 36.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

3-(2,2-Dimethyl-1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-5-(5-formyl-3-thienyl)-1H-indole-7-carboxamide (30 mg, 0.070 mmol) was dissolved in dimethyl sulfoxide (1.5 mL) and put in a microwave vial. The mixture was stirred and 1-2 drops of acetic acid and azetidine (0.047 mL, 0.697 mmol) was added. The mixture was left stirring 30 minutes at 23° C., before adding sodium triacetoxyborohydride polymer bound (299 mg, 0.697 mmol). The vial was sealed using a silicon septum, and the mixture left stirring 16 h at 23° C. Based on LCMS only 60-70% of conversion was observed. The sodium triacetoxyborohydride polymer bound was removed by filtration. The crude product was purified by preparative HPLC (NH4OH buffer). The desired fractions were concentrated, giving 12 mg of the title compound.

Workup

  1. waitThe mixture was left
  2. stirringstirring 30 minutes at 23° C.
  3. customThe vial was sealed
  4. waitthe mixture left
  5. stirringstirring 16 h at 23° C
  6. customThe sodium triacetoxyborohydride polymer bound was removed by filtration
  7. customThe crude product was purified by preparative HPLC (NH4OH buffer)
  8. concentrationThe desired fractions were concentrated

Sources & evidence

ORD record
ord-b3be59e5cf314f2badbc80532e37cfff
Source dataset
uspto-grants-2011_12
Patent number
US08071584B2

Reaction notes

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