Dimethylamine → HCID 25072551, compound

HRID 656146Notes

Reaction equation

HRID 656146 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].[CH3:30][NH:31][CH3:32].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CS(C)=O.C(O)(=O)C>[CH3:30][N:31]([CH2:22][C:20]1[S:19][CH:18]=[C:17]([C:14]2[CH:15]=[C:16]3[C:11](=[C:12]([C:24]([NH2:26])=[O:25])[CH:13]=2)[NH:10][CH:9]=[C:8]3[CH:6]2[CH2:5][CH2:4][S:3](=[O:27])(=[O:28])[C:2]([CH3:29])([CH3:1])[CH2:7]2)[CH:21]=1)[CH3:32]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 59332756HCID 59332756, compound

Product 1

HCID 25072551HCID 25072551, compoundYield 37.3%

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 was added, dimethylamine (0.348 mL, 0.697 mmol) was added. The mixture was stirred 2 hours 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 overnight at 23° C. The sodium triacetoxyborohydride polymer bound was removed by filtration (syringe filter 45 um). The product was purified by preparative HPLC (NH4OH buffer). The desired fractions were concentrated, giving 12 mg of the title compound.

Workup

  1. stirringThe mixture was stirred 2 hours at 23° C.
  2. customThe vial was sealed
  3. waitthe mixture left
  4. stirringstirring overnight at 23° C
  5. customThe sodium triacetoxyborohydride polymer bound was removed by filtration (syringe filter 45 um)
  6. customThe product was purified by preparative HPLC (NH4OH buffer)
  7. concentrationThe desired fractions were concentrated

Sources & evidence

ORD record
ord-b9c46315d2e5495f9a54556f01d700d5
Source dataset
uspto-grants-2011_12
Patent number
US08071584B2

Reaction notes

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